Chicago | 3-Day Itinerary & Visual Travel Guide
Going into this trip I thought 3 days in Chicago would allow me to see most of the city but I deeply underestimated its size. I now realize it was naive of me to think this; after all, Chicago is America’s third largest city.
Not only was I taken aback by the size, but I soon realized that Chicago has a rich history and passion for design and architecture. I loved that even though the neighbourhoods were spread out, it still felt walkable. And while I spent some time in the Loop (Chicago’s downtown core), I tried to get out and explore the South, West and North sides as well.
I’m sharing some of my highlights and travel tips so you can make the most of your visit. I’ve also included recommendations for accommodation and food - and yes, I’ll share where you can get yourself a delicious Chicago deep-dish pizza. This Chicago trip planner should act as a guide to help you create your perfect itinerary.
GO IF YOU LIKE:
ARCHITECTURE | ART | WATERFRONT views | epic SKYLINEs | WALKABLE CITIES | SAUCY PIZZA
Itinerary At a Glance : 3 Days in Chicago
DAY 1
Morning: Breakfast at The Allis Chicago
Late Morning: The DuSable Museum of African American History
Lunch: Avec Restaurant
Late Afternoon: Millennium Park
Sunset: John Hancock or Willis Tower
Dinner: Girl and the Goat
DAY 2
Morning: Logan Square Farmers Market
Late-Morning: Walk the 606
Lunch: Pequod’s Pizza for a Chicago deep dish pizza
Afternoon: Walk off the pizza in Lincoln Park
Late-Afternoon: Walk the Riverwalk
Evening: Chicago Architecture River Cruise
Night: Crown Fountain in Millennium Park
DAY 3
Morning: Cloud Gate and Millennium Park, walk the Lakefront to the Adler Planetarium
Late-Morning: Take a water taxi to Chinatown
Lunch: Eat fresh dumplings in Chinatown
Afternoon: Visit the Art Institute of Chicago
Evening: Sunset cocktails and dinner at Cindy’s Rooftop
Expand the legend in the map for my detailed Chicago itinerary
The map includes additional sights and restaurants
Double check opening times and reservation requirements at restaurants
Shopping: My itinerary doesn’t include shopping but I have marked some sustainable boutiques on the map below. Most other big-name brands tend to be located on Magnificent Mile.
Some links below are an affiliate link, meaning, at no additional cost to you, I will earn a commission if you click through and make a booking. In addition, And Then I Met Yoko is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for me to earn fees by linking to Amazon and affiliated sites at no additional cost to you. As always, I only recommend products and services I trust.
Day 1
Visit the DuSable Museum of African-American History
DuSable Museum Collections
Inside the DuSable Museum are permanent exhibitions that cover a wide-range of African-American history. There is a wing dedicated to prominent South sider, Margaret T. Burroughs (founder of the museum), who influenced art and culture within the city.
We’re given insight into Harold Washington, Chicago’s first African-American Mayor who lived to serve a short term but inspired large voter turnout.
My favourite section was about the citizen soldiers of the Fighting Eighth - an Illinois infantry who fought in the First World War. This exhibit was filled with photography and memorabilia from the war like handwritten letters from the soldiers.
We’re also taken on a journey through the different periods of history, from slavery, to the civil rights movement and into present-day politics and culture. There are inspiring stories about Harriet Tubman and Martin Luther King juxtaposed with the Jim Crow laws and KKK robes.
The museum starts with a single quote,
“what will be your legacy?”
The Red Summer of Chicago
In the early 20th century, Chicago received an influx of African-Americans fleeing persecution in the South as part of the Great Migration. This movement sparked racial tensions in the city and after a young African-American, Eugene Williams, was killed in the summer of 1919 the city saw months of violent riots.
100 years later the DuSable Museum has an exhibit which talks about the timelines and outcomes of these events. If you can’t make it out to the museum I suggest learning about it on this podcast.
My Experience in the Museum
The majority of my visit was quiet, with only a few other guests visiting around opening hour. This was a stark contrast to The Chicago Art Institute which was packed with people. I loved the content in the museum and could only imagine how much better it would be with more funding.
Similar to my trip to Savannah, I found myself once again digging through travel guides to find places where I could learn about local African-American history. I’m glad I found this museum.
Nearby Sight: President Barak Obama’s Family House
Only a 15-minute walk from the museum is President Barak Obama’s family house. Still heavily guarded and covered by trees it was cool to see where he lived before becoming President of the United States. If you’re up for a calm walk through a mainly residential area, it’s worth it.
Explore Millennium Park
A little bit about Cloud Gate
Cloud Gate (aka, the Bean) was designed by Indian-British artist Anish Kapoor. The photogenic sculpture is a seamless 110 ton masterpiece. It reflects everything around it, including Chicago’s skyline, in a quirky and distorted way.
In the evening I noticed it suffered from dirty handprints but the next morning it was clean. Apparently it gets a wipe down twice a day and an annual wash with soap.
The reality of The Bean
Let me start by answering the obvious question - I shot these photos at 6am, just as the sun was rising. At that time there were already a handful of photographers and eager tourists. It is virtually impossible to get a solo moment with this iconic piece of Chicago but if you wake up early enough you will get close.
I also visited The Bean on a Saturday night and it was so packed with people that I immediately left. I didn’t really appreciate how cool it was until the next morning, when I could wander around it in peace and quiet. It’s no wonder photographers love coming here because every angle provides a fantastic picture.
I share more tips on shooting this below.
Jay Pritzker Pavilion
This very cool outdoor stage was designed by Frank Gehry. Not only are the acoustics phenomenal, but it’s set against the backdrop of Chicago’s skyline which is even more impressive.
There are often outdoor concerts in the summer months. While I was visiting in early September, it was the Chicago Jazz Festival and the park attracted thousands of people who came for picnics and to enjoy the music.
For updates on events visit their website.
Visit The Crown Fountain at Night
The Crown Fountain is only a few minutes away from The Bean in Millennium Park, but it’s a must-see, especially at night time. Designed by Catalan artist Jaume Plensa, the fountain has two opposing walls with digital screens. These display video of the faces of over 1,000 different Chicago residents, showcasing the diversity within the city. Between the screens is a large reflective pool of water - which barely covered the top of my feet. Roughly every 10 minutes the faces would purse their lips and start to spew water.
This is obviously a popular spot for kids, especially in the hot summer months. There’s lots of running and splashing. I took off my shoes and went it. It was a bit chilly at first but I loved the perspective from the center of the fountain.
Enjoy the city from the 360 Observation Deck
There are two popular towers which give epic views of Chicago, The 360 Observatory at the John Hancock Center and the Willis Tower (formerly Sears Tower). I opted for the John Hancock building because I wanted to see Willis Tower. Additionally it’s closer to the lake and has views of Navy Pier.
As stated in its name - this observation deck offers a 360 degree view of the city. We’re able to see downtown, the lake and the sprawling suburbs into the North and West of Chicago.
If you’re an adrenaline junkie you may enjoy the “Tilt”. This attraction requires an extra pass and it allows you to stand in a glass box as it’s tilted off the side of the building. Not my cup of tea but others seemed to be enjoying it.
Some facts about the 360 Chicago Observation Deck
It has 94 floors and is the 4th tallest building in Chicago
It has 1,632 steps
It is 314 meters tall (1,030 ft)
Pro Tip: Fast Passes are Useful during Peak Times
I’ll be the first to admit, I didn’t do proper research and got screwed overpaying. Firstly, when we arrived the line was almost out the door and this was only the visible part of the line. I asked for a rough time estimate and was told 2 hours. HA!
Considering I didn’t have the option to come back another day, NOR was I willing to miss sunset, I paid an excruciating $35 entrance fee to get the Fast Pass.
Though it was pricey, the Fast Pass got me up in 20 minutes. I was given priority and was ushered into a second line which jumped in front of everyone.
A few things to note:
- If you’ve already purchased tickets you can upgrade them to a Fast Pass at the ticket office
- There is a bar at the observation deck which apparently you can go to for free. You just need to pay a $5 entrance fee and purchase drinks. I read the drinks are roughly $15 but this would have been a good option to avoid the line and Fast Pass fee.
- I opted to come for sunset so I could photograph the city with and without sunlight. My photography notes can be found below.
- If you’re visiting during the summer there are fireworks at Navy Pier (on Wednesday and Saturday nights). If you’re at the observation deck at night and time things right, you’ll be able to catch front row seats to the fireworks at a unique angle. The schedule can be found here.
- If you already have a CityPASS then you have the option to use it for 360 Chicago and get fast tracked.
Day 2
Grab Breakfast at Logan Square Farmers Market
Logan Square is a neighbourhood in the North-West of Chicago which runs a weekly farmers market from 10am-3pm every Sunday. During the warmer months (roughly May - October) the market is outdoors. During the colder months the market moves indoors (roughly November - April).
The market has a ton of local vendors, and it’s best to show up at 10am before things get picked over. Grab some pastries and have yourself a breakfast on a nearby bench.
Pro tip: Come prepared for the farmers market
Though they had Nitro cold brew coffee, I didn’t find any hot coffee vendors so I grabbed something at Gaslight Coffee Roasters instead
Enjoy breakfast at Logan Square where they have benches
The Farmers Market is very dog friendly
There is a stall that is equipped for credit card purchases. This means that if you want something at a vendor that is cash only, you can get a credit slip, pay at the credit card station and return to your vendor with the payment. So if you don’t carry cash, you can still enjoy the market. With that being said, cash is certainly better for you small-business vendors :)
If you plan on doing some serious shopping, bring some reusable bags
Walk the 606
Walk off the farmers market on the 606, a highline that used to be an old railway track and is now a 2.7 mile long walking/bike path with green spaces.
I told myself I wouldn’t compare Chicago to New York but if you’re a fan of the Highline in New York City then you will enjoy the 606. The path connects neighbourhoods like Logan Square, with Humboldt Park, Bucktown and Wicker Park. You won’t find many tourists here either. Just locals getting in their exercise, catching up with friends or walking their dogs. There are trees planted along the way and street art on the sides of buildings. This walk really gives you a flavour of local life in the city.
Planning for the 606
Open from 6am-11pm
The 606 can be entered through several access points - download a printable map here
There is a cycling lane which takes up the majority of the space. Walking and running lanes are on the edges.
Eat Pequod's Deep Dish Chicago Pizza
We have come to the point in this blog post where I talk about Chicago’s famous deep-dish pizza. What can I say, it’s delicious and you need to try it. Asking locals for their favourite pizza is likely to result in a war and added confusion. Some like their pizza super saucy, others prefer flaky crusts, some like caramelized toppings… it’s about as subjective as art.
With that being said, three names seemed to be reoccurring among the people I asked: Lou Malnati’s Pizzeria, Uno Pizzaria and Pequod’s. Since I didn’t have the luxury of being able to try all three I went with the one that garnered the most votes - Pequod’s. After a helllllllllla long wait to get in we eventually were served the pizza.
I ordered a classic pepperoni, with extra cheese - a small is enough for two people.
Verdict
The sauce was tangy and delicious. I ordered it with extra cheese so it came nice and gooey in the center. The crust was flakey and all the textures worked well together. It was cooked perfectly, with the cheese and pepperoni slightly charred.
Pro Tip: Planning for the Long Line
When I arrived at Pequod’s I was lucky, I wasn’t too hungry. I waited over an hour for a table then an additional 45 minutes to get the pizza (which is normal based on the cooking method). Because this spot is so popular they have a good waitlist system which allows you to enter your phone number and refresh to see where you stand in line. I started at 38th (yikes). The waitlist allowed me to explore some of the nearby shops (there’s a clothing consignment store and book store).
What I realized later was that Yelp! allows you to join the waitlist before you get there. This would have saved a ton of time!
Find peace in the Lincoln Park Conservatory
The Lincoln Park Conservatory was build out of a desire for residents to escape the industrialization of the city. Today you can wander through 4 different sections: The Palm House, Fern Room, Orchid House and Conifer Garden. Each room has signage for the different trees, ferns and flowers and regardless the time of year, it’s going to be filled with lush greenery.
I went into this visit with low expectations but found myself quickly falling in love with this place. While there were lots of people also visiting, I found a sense of calm and clarity in the conservatory. I’m not sure if it was the added oxygen or just feeling like I’d escaped the madness of the city, but I felt at peace. I could only imagine how much better it would be during low season with less people.
Planning your Visit to the Lincoln Park Conservatory
Hours of Operation: 9am-5pm every day of the year
Price: FREE (unless there is a special event)
Wander Lincoln Park and see some Animals
Right outside the Lincoln Park Conservatory is Lincoln Park itself. It’s a great place to stroll through and have a picnic. There are ponds, grassy areas and it connects to the Lincoln Park Zoo.
I am actually not a fan of zoos (the whole animals in captivity thing) so I didn’t plan on visiting. But to my surprise you can’t really avoid it. I had to walk through parts of the zoo to get to the park. This means, you guessed it, it’s free and open to the public. So while I didn’t plan on seeing the animals, I kind of stumbled upon some flamingoes and zebras.
There are also alpacas, bears, monkeys, camels, rhinos, hippopotamus, giraffes, polar bears and more… in case you’re interested.
Walk the Chicago Riverwalk
The Chicago River is a really fun place to people watch. You can grab a drink or some food from one of the many restaurants with views of the water. If you’re looking to save money, you can simply sit on the free steps. Either way it’s nice to relax and watch the boats and people pass you by.
Fun Activity: Chicago Electric Boat Company
If you’re with a group, a fun activity is renting an electric boat and touring around the Chicago River. No need to have any boating experience for this either! They say it goes about the speed of a golf cart and is easy to maneuver. Because the boats can fit up to 12 people and are paid for by the hour, it’s a fun activity to do with family or friends. If you’re ok shelling out the money, it makes for a romantic couples trip too.
Say Hi to Chicago’s iconic Buildings On the Architecture Boat Cruise
When I asked people what I should do in Chicago, absolutely every person said, “go on the architectural boat cruise”. So I did. This 90-minute cruise took me along the three branches of the Chicago River, passing iconic buildings like The Willis Tower, Civic Opera House, Goose Island, Marina City and much more.
Our tour guide, Carol, was a volunteer from the Chicago Architecture Center and an avid architecture fan. She shared details about the history and engineering of the buildings, often making parallels between them and people. It was a clever way to make architecture relatable to everyone.
What really surprised me was the range of architecture in Chicago. Each building reflects different decades. We saw French influence and beaux arts with ornate wreaths and garlands, right next to contemporary, post-contemporary, modern, art deco, and post modernism.
I took the Twilight River Cruise which isn’t ideal for photography but offers views of the city as it lights up for the evening (photography tips below).
Preparing for the Architecture River Cruise
Cost: $44.48 and $49.21 for the twilight cruise
Duration: 90 minutes - arrive 30 minutes before to line up for a seat and board
Seasons: Runs from the end of March until the end of November
The facilities: There is a full-service bar on the boat which offers cocktails, beer and wine. There are also restrooms and a climate-controlled indoor room in case you need to escape the heat/cold.
Day 3
Walk the Lakefront to the Adler Planetarium
In case you missed it, Chicago sits right on Lake Michigan. This means that within a few minutes you can escape the crazy downtown core and find yourself on a peaceful walk along the lake. If you’ve got the energy, I highly recommend walking to the Adler Planetarium (about 45 minutes from Millennium Park) which is where you’ll get stellar views of the entire Chicago skyline. You’ll pass the Shedd Aquarium on the way there which is another interesting Chicago building.
Head there early in the morning to find yourself alone with some seagulls; it’s divine and feels like one of those wonderful hidden gems.
While I didn’t have time to actually visit the Adler Planetarium it looks like a good spot to bring kids. And if you’re craving exercise, the lakefront is a great place for a morning jog. At least that’s where all the locals seem to go.
Take a water taxi to Chinatown for Dumplings
What better place to enjoy fresh dumplings than Chinatown. In the South Side of Chicago, just off the river is a neighbourhood which is home to over 50,000 people. It’s easy to access Chinatown from the subway, but if the weather is nice, try the Chicago Water Taxi.
The Chicago Water Taxi
The water taxi service has 7 different stops that run along the Chicago River. The stops are concentrated mainly in the central loop but go as far South as Chinatown and as far North as Goose Island. The taxi services run when the weather is good, ending around Thanksgiving. While they’re rarely sold out, they are busy in the summer months.
Just be careful, my tickets weren’t checked and I boarded the wrong boat. Luckily a last-minute passenger came and asked where the boat was heading and when I heard the answer I quickly jumped off and got on the correct boat. In my opinion, the signage isn’t clear and I should have been given better instruction from the staff.
Chicago Chinatown
The water taxi docked at Ping Tom Memorial Park which is a small park that overlooks the river. It’s a bit strange, but you have to walk through some residential areas before getting to the heart of Chinatown.
We eventually stumbled upon a long commercial strip which was filled with restaurants, bakeries and stores. I made a reservation to Qing Xiang Yuan Dumplings. QXY Dumplings make fresh dumplings with an array of fillings and cooking methods (more about it here).
Don’t stop there though, just a few minutes away from the strip (towards the subway stop) and you’re greeted by Chicago’s Chinatown Gateway. Once you pass here you’ll find more restaurants and small shops selling Chinese knick knacks and K-Pop paraphernalia.
Get lost at the Art Institute of Chicago
Like the Louvre in Paris, the Art Institute of Chicago is somewhere I could have easily spent several days. The sheer size - four floors sprawling with collections - exhausted me and at times I was left disoriented. All that to say, it’s easy to spend a day here and if you don’t have that kind of time, accept that you’ll come back for a second visit.
What to expect at the Art Institute of Chicago
While the majority of the museum focuses on paintings, there are also incredible sculptures, medieval armour, swords, rifles, jewelry, furniture, photography, paperweights, textiles and my favourite - the miniatures room! This gallery is filled with dollhouse-sized room displays that show how architecture, decor and furniture styles changed throughout the world and periods in history.
The collections in the museum are not American specific either. They cover the ancient cultures of Asia, Africa, Islam, Europe and the Americas. The art has an international focus too as it moves through Impressionism to Contemporary and Modern Art.
I’m someone who spends little time in art museums but I really enjoyed this one.
Some of the Highlights
American Gothic - Grant Wood
The Old Guitarist - Pablo Picasso
A Sunday on La Grande Jatte - Georges Seurat
Stacks of Wheat - Claude Monet
Liz #3 - Andy Warhol
The Bedroom - Vincent Van Gogh
Two Sisters - Pierre Auguste Renoir
Pro Tip: Planning for your Visit
There are audio guides for rent however the Art Institute has a brilliant app which gives you detail on some of the important pieces. You can download the app for iOs and Android here. There are also guided tours which are free and run every day at noon and 2pm.
You are encouraged to take photography and share it, however no flash is allowed. Tripods, video and selfie sticks are also not allowed.
You must check your backpack for $1 in the coat check area. Your bags cannot have food and liquids inside, nor can you bring these items with you into the museum. I ended up chugging my entire bottle of water in line.
Hours of operation: Open every day of the week, 10:30am-5:00pm (Thursdays closing is 8:00pm). Closed on Thanksgiving, Christmas and New Year’s Day.
There are sometimes special exhibits. Unless you’re dying to see these exhibits you can pay the general admission and be spoiled for choice with the permanent collections.
There are a few restaurants and cafés within the gallery where you can refuel.
The line wasn’t too long when I visited but if you want to skip it you can purchase a FastPass for the Chicago Art Institute.
The Museum of Contemporary Photography
This little gallery is free to enter, but they politely ask for a donation. Let me start by saying, it’s contemporary photography, which like all art, is quite subjective. Most people either love it or hate it. As a photographer I enjoy all types of photography, so I had a good time wandering this gallery - my husband, not so much.
If you’ve got the time and you’re interested in photography, I’d suggest giving it a try.
For Next Time
Sadly my weekend went by quickly with so much more I wanted to see. If you’ve got more time, consider adding a few of these attractions to your itinerary.
- Skydeck Chicago - Inside the Willis Tower is the observation deck that gives you 360 views of the city. If you’re brave, you can step onto “The Ledge”, a glass box that juts out over the side of the building.
- The Adler Planetarium - great for kids
Chicago Architecture Center - Dive deeper into the architecture of the city. It includes 3D models with details on the engineering of some of Chicago’s most iconic buildings.
Chicago Athletic Association - A hotel in the downtown core that’s filled with great food and drinks; including Cindy’s, a famous rooftop patio. Make reservations for this one, I couldn’t get in last minute.
Navy Pier - A large pier that is filled with rides, galleries, food and drinks. A bit kitschy but lots of people are into that.
Chicago History Museum - For all you American history buffs
- Chicago Hot Dogs - An iconic staple food that I sadly missed. I planned on having mine at U.B. Dogs.
- Live Entertainment - Catch a show at the iconic Chicago Theatre, some live music at The House of Blues or some sketch comedy at Second City Chicago.
- Sports - Chicago has them and I'll get in a lot of trouble if I don't mention it. Firstly, there are two, yes not one but TWO, baseball teams in Chicago. The Cubs (North Side) and White Sox (South Side), yet another topic that will surely spark a passionate debate. If baseball isn't your thing you can catch a Chicago Bulls basketball game or Blackhawks hockey game or The Bears if you want some football action.
“And don’t forget to look up.”
Where to stay in Chicago
I try not to compare Chicago with New York - locals don’t appreciate it - but when it comes to accommodation, Chicago differs greatly. You can get a reasonably priced hotel in the downtown core for under $200 a night, which is virtually unheard of in New York City.
I stayed at the Kimpton Hotel Allegro, I chose it because of the location and the fact that I could use my rewards at this hotel chain. I found the concierge friendly and helpful. He would text me throughout the day to see if I needed anything. The rooms were large and clean and the location is central (7 minutes from Millennium Park).
Verdict
I enjoyed my stay and recommend it to fellow travellers; however, I do think there are comparable and cheaper options which provide better value. Check them out in my “Affordable Comfort” section below.
Budget
These budget hotels will draw a younger crowd but the prices just can't be beat.
Freehand Chicago
FieldHouse Jones Chicago
Hotel Lincoln, a Joie de Vivre Hotel
Modern River View Apartment
Affordable Comfort
These are some well-rated and centrally-located accomodation. They offer high-end service and comfortable ammenties at afforable prices.
Virgin Hotels Chicago
Hotel EMC2, Autograph Collection
The Blackstone, Autograph Collection
Viceroy Chicago
Luxury
Looking to splurge? These are some well-designed and highly-rated options which have central locations. Prepare to feel fancy.
Chicago Athletic Association
The Langham Chicago
The Publishing House Bed and Breakfast
The Peninsula Chicago
Where to Eat in Chicago
Avec Restaurant
Mediterranean | $$ | MY FAVOURITE
I’m a sucker for a mediterranean restaurant with shareable plates and Avec is exactly that. This was my favourite meal in Chicago. Every dish was flavourful - my proof - I sopped up all the sauces with the warm, fresh bread. They don’t hold back on the spices either!
The added bonus is that Avec clearly has a passion for wines and they serve some delicious ones. So even if you’re not hungry, coming for a nice glass of wine is enough.
The one watch out is that the restaurant is tiny and fills up quickly. Make a reservation to avoid disappointment.
Qing Xiang Yuan Dumplings
Dumplings | $
I had really high hopes for QXY Dumplings and let me start by saying, they were delicious. You could order them in an array of fillings like beef and onion, lamb and coriander, pork and shrimp and then decide on how you want them cooked (boiled, steamed or pan fried). I often asked the servers for recommendations and wasn’t let down by their selections.
The dumplings come in two sizes (medium-12 pieces and large-18 pieces). This serving size was annoying because we were only 2 people so it limited the varieties we could try. We ended up getting three mediums but there were so many other fillings we wanted to try.
The other thing to mention is that this place has crazy fast turnaround. If you’re looking for a quick meal then you will love it but if you want to relax over a long meal this is not the best place. I felt stressed when I was there, I found the manager hovered around our table and as soon as we finished a plate he would be signaling the servers to come clean up. Again, it’s not bad if you want a quick meal, but I felt like they just wanted us to hurry up and be gone. They also wouldn’t let me drink my bubble tea which I brought from another restaurant.
Overall, go if you want quick dumplings, because they were delicious, but don’t go if you want a long, leisurely meal.
Make a reservation here or you may have to sit with strangers at a communal table.
Other options in Chinatown
While the dumplings were the reason I went to Chinatown, I also grabbed some other delicious foods. Bubble Tea at Joy Yee and matcha-flavoured pastries at Saint Anna Bakery. There are other tons of delicious Asian foods in Chinatown like dim sum, hot pots, noodles, bbq… the list goes on!
The Allis
Brunch/Salads/Sandwiches | $$
The Allis is part of the Hotel, Soho House Chicago. I enjoyed brunch here though they serve food all-day long. The interior is bright and airy, thanks to their floor-to-ceiling windows. I had the grilled halloumi and cauliflower wrap and my husband had the French toast. If you like French toast - get the French toast!
Find their contact information here.
Logan Square Farmers Market
Pastries/bread/buns | $
This Farmers Market is a great place to come for breakfast but you’re going to want to get there early enough to score some of the delicious baked good before they get picked over.
I stocked up on a croissant, raspberry icing donut and muffin at Letizia’s Natural Bakery. I also grabbed an adobo pork bun at Pecking Order - this was my favourite.
Find the hours of operation here.
Garrett's Chicago Mix Popcorn
Popcorn | $
You haven’t had popcorn until you’ve had Garrett’s Chicago Mix. Chicago Mix is a weird mixture of cheddar and caramel popcorn. Yeah - I know - bare with me. The sweet and salty blends so well together, it’s the only way I eat popcorn these days.
I’ve also had Chicago mix, purchased at the grocery store, but getting a fresh bag of popcorn from Garrett’s is substantially better. The kernels are buttery and not dry like store-bought popcorn. I miss it already.
When to visit Chicago
Summer
I asked locals and they all say, summer in Chicago is the best time to visit. The weather is obviously warmer and this opens up a ton of activities on the lake and river like cruises and kayaking. You can picnic, head to the beach and enjoy outdoor patios. Of course this comes at a price, like higher hotel rates and more crowds.
Winter
Chicago is cold in the winter, obvious statement I know, but add the strong winds from the lake and it can be downright painful. All that being said, winter has its perks. If you come late November and December the city is in full Christmas mode with decorations and lights flooding Michigan Ave. Outside this peak time, you’ll be able to save money on accomodation and do winter activities like skating.
Autumn
September and October would be my vote for visiting Chicago. The trees will be changing colour (peaking around mid-October), the weather will be cooler which means you can layer comfortably and you’re less likely to get rain like you would in the spring. There will also be less crowds than the summer.
Spring
The weather gets nicer in the spring with highs in the high-teens. This is a great time to visit before the crowds and spiked prices of the summer but chances of rain are higher so be prepared to supplement your trip with indoor activities and don’t forget your rain jacket.
Transportation in Chicago
From the Airport
Once you make it to either of Chicago’s airports a train ride into the city is straightforward. Just follow signs for the trains, you can purchase your ticket at the station. Trains are the best way to get to/from the airport from downtown.
Public Transport
Part of the Chicago experience is taking the CTA (Chicago’s public transit system). These are mainly above-ground trains which run regularly and connect the downtown core with some of Chicago’s suburbs. Note: the term “subway” only applies to the red and blue lines which run underground in the city.
Like most big cities you may encounter some strange people on the train. I had a guy walk on mine dressed in full Jesus attire, holding a body-sized cross. It was a good initiation to say the least.
Overall the CTA is an efficient and economical way to get around. Here’s a useful map to print out and bring with you.
ride Share
If you want to get from point A to B fast and are far from a subway station then Uber/Lyft are good options. Since three days in Chicago is short, I found myself using them frequently.
Divvy Bike
Biking is a popular way to get around the city, especially if you plan on going along the Lakefront or on the 606. You can rent Divvy Bikes and pay for short rides or day passes. Information and pricing can be found here.
Pro Tip: Use the Divvy Bikes App
In order to find the docking stations and see how many bikes are available it’s best to use the Divvy Bike app. Otherwise you can get the information on their website.
Safety In Chicago
Chicago is a relatively safe city but like any big American city there are pockets of places you don’t want to be venturing at night. Generally, the downtown core and locations mentioned in this guide are safe to visit.
I often heard about “The South Side” of Chicago being somewhere to avoid so I asked my concierge about it. He said it really depends where in the South Side you go. Chinatown was fine and Washington Park, home to the DuSable Museum and the neighbourghing Hyde Park were lovely areas. I walked freely through them during the day and felt fine. I have read that West of Washington Park, heading towards Fuller Park can be a bit rough so you may want to avoid wandering in that direction.
A lot of neighbourhoods in Chicago are going through gentrification. It’s common to find yourself in an area that feels industrial with dilapidated buildings but has a thriving restaurant and bar scene. Logan Square is a good example of this.
Photography Tips for Chicago
The Bean
Getting there for sunrise will have less people but in early September it wasn’t until the latter half of Golden Hour that the sun really started to provide interesting light. This monument really is fun to shoot, so grab the classic angles then go around and experiment. You can walk under the Bean and get up close. Later in the day you can expect heavy crowds. It may be frustrating but consider using the crowds to your advantage and capturing the full scene or how people interact with the monument.
John Hancock Tower
Tripods are not allowed, though I saw someone using one and was really ticked off that they were allowed to bring it up. They do allow monopods and GorillaPods (see below). The observation deck has “Tripod Mondays” which is the best time for photographers to come. I didn’t have a tripod but I found a few spots on the ground and steadied my camera that way. Polarizers may help with the glare from the window.
The Architectural Boat Tour
Try to time your tour during golden hour. Once the sun sets it becomes quite difficult to shoot handheld. Try to get a seat along the edge of the boat. You will be able to use the railing to steady your hands if shooting in the evening. Since the boat turns around in all the directions, either side of the boat works. You are free to get up and move around too, so don’t feel like you have to stay in your seat.
Chicago Skyline at Adler Planetarium
Bring a tripod and ND filter - If you want to do some beautiful long exposure. The early morning generally has less waves but you never know. Chicago is known as the windy city and I’ve seen instances where the waves are pretty strong for a lake.
Consider a panoramic - The view from the Adler Planetarium lends itself nicely to a panoramic. The one above in my post was done stitching together 7 portrait shots.
Consider a polarizer - To help with the glare from the water
Sunrise - Shoot in the morning if you want the sun to light up the skyline (my shots were done about an hour after golden hour, it would have been much better during golden hour)
Sunset and Blue Hour - The sun will backlight the skyline and blue hour will be awesome with the buildings lit up
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