How to Spend Two Days in Chicago

Chicago, on Lake Michigan in Illinois, is among the largest cities in the U.S. Famed for its bold architecture, it has a skyline punctuated by skyscrapers. Two days in the city offers a chance to try some of the most iconic foods, unique history, speakeasies, and more.

I’ve officially been to Chicago in every season but fall and have to say – spring might just be my favorite. I absolutely loved this trip to Chicago and highly recommend taking the time to spend a few days here. You can see most things in just 2 days, but could definitely spend longer.

As someone who’s been several times, this is definitely a perfected itinerary that gives you a bit of everything. There’s tons of fun and cheap things to do in Chicago and I may have found the perfect way how to spend two days in Chicago.

Table of Contents

Note: If you want to book a hotel in Chicago that won’t cost $1000 for the weekend (literally), book far in advance! We looked a month out and had no options. We ended up staying at a shared Airbnb that had an on-suite bathroom just a 10-minute drive from downtown. Even that was $100 a night! 

Day 1

Okay so this day is going to seem really packed! But here’s the thing – we were running out of things to do on this day because everything was really close together and is more about seeing the sites than doing an activity. We had hours of free time between activities which meant day drinking and relaxing (perfectly fine with me!).

Hero Coffee

Hero Coffee is a local coffee chain found throughout Chicago. We found this cute spot right downtown in a cool alley way and it was a relaxing first stop for a coffee and chocolate croissant.

Chicago Theater

Armed with iced coffee, we walked a few blocks to the Chicago Theater. This is a must see and if you have time, definitely go see a performance. We checked online but nothing was happening while we were there.

The Chicago Theater is famous for many different reasons. First, it has a beautiful facade and has hosted so many famous musicians and performers. It was also host to some of the most extravagant parties Al Capone held during his days in Chicago. This was along our walk so it was an easy stop. We also went by here later on our ghosts tour.


Millennium park

Millennium Park is large and beautiful. We loved walking around and seeing all the beautiful views of the city from inside the park. “The Bean” is the most famous piece of art in the park and worth the stop! At 10 am it was already extremely packed but we did get to snap a good selfie and walk through.

Make sure you walk through the bean for some really cool reflections and views. The buildings reflecting off of it were stunning as well.

Navy pier

From Millennium Park we walked to Navy Pier. In my mind, this stop is a must while in Chicago because it gives the best view of the city and some fun. It’s home to the Children’s Museum, boat tours, lots of restaurants, shops, and rides.

Fun fact – did you know the Ferris Wheel was invented in Chicago? They created it for the World’s Fair in 1883. At first they considered creating a larger version of the Eiffel Tower, but as Americans do… they wanted to be different! So a guy named George Ferris came up with the idea of a giant spinning wheel people could ride on. The original Ferris Wheel was not at Navy Pier but it is cool to ride one where the Ferris Wheel was invented.

The Ferris wheel is probably my favorite ride on Navy Pier. I first road the Ferris wheel at Navy Pier when I was 9 and so riding it again was so special! Plus since it was invented there, you feel like you are a part of the history! The views were gorgeous which is definitely an added bonus (and I’m all about a good view!).

Pro-tip: Bars on Navy Pier offer alcoholic drinks to go. You can actually drink anywhere along the pier freely. Yes please! We took advantage of this after our Ferris wheel ride relaxing as we were waiting for lunch.

Deep dish

Deep dish pizza is a famous dish invented in Chicago. It’s more rich than your typical pizza and fills you up quick. If you choose to go somewhere downtown, even for lunch, you will most likely end up with a wait. We put our name on the list at Giordano’s Navy Pier location and the wait was 1 hour. There are lots of bars though so we grabbed a drink while we waited.

Chicago style deep dish has the cheese, and things we typically think as toppings, underneath a layer of sauce. It is cooked in an extra deep pan (surprising given it’s name right?!) and is very filling. With three of us, we ordered a medium plus an appetizer and ended up with a piece left – more filling than your typical pizza.

Chicago riverwalk

After lunch we were full and needed to walk off the giant pizza we ate! It was time to walk the riverwalk that is just stunning. Chicago is built along a river, and the views are just gorgeous! Walk along the water and across bridges for great views (there are many). City Winery has a great spot on the water with tables and delicious wine to take in the views.

We again took some time to relax along the waterfront and enjoy the epic views (are you seeing a pattern?! Tons of great views in Chicago).

Gangsters and Ghosts Tour

I always like to fit in a little history while in a city and the gangsters and ghosts tour was the perfect way to do it. We spent about 2 hours walking around and checking out the spots that are most famous for, well, gangsters and ghosts!

During the tour, we got the chance to see some of the most famous buildings in Chicago as well as hear the history. We walked from the riverwalk to the Chicago theater to more. Chicago has a history, especially with prohibition and the industrial revolution so I highly recommend going on this tour if you want to hear some of the secret and interesting history of the city.

Portillo’s

The other food Chicago is famous for is the Chicago dog. The hot dog is topped with yellow mustard, chopped white onions, bright green sweet pickle relish, a dill pickle spear, tomato slices or wedges, pickled sport peppers and a dash of celery salt. One of the top spots, Portillo’s, ended up being right near a speakeasy that was recommended to us on our tour. We knew we had to check it out!

Portillo’s has many different counters and you can order hot dogs, brats, and more at the different counters. It can get very crowded during the day, but has ample seating and space for people to relax. We were there later in the evening around 8 and so it was not crowded at all.

It was so delicious and their French fries definitely hit the spot too.

The Drifter – An Original 1920s Speakeasy

We ended up choosing this speak easy because it was close to where we were, but also, came highly recommended. It’s located in the bottom of the Green Door Tavern. You have to go through a bookcase next to the bathrooms in the basement. It was a working speakeasy all the way through the 1920s prohibition and they have kept the vintage feel of the bar.

All the drinks are listed on tarot cards, and my boyfriend couldn’t stop ordering the Miz McFlury because it was so good (okay, fine, I ended up ordering it too because YUM!). They also have live entertainment nightly and if you want to see what a speakeasy was like, this is the spot to do it.

Godfrey Hotel Rooftop Bar

We walked just two blocks over to a rooftop bar to get another great view (surprise!). The Godfrey was the perfect spot to take in a view, even though it was cloudy, and grab a final drink before Ubering home.


Pro-tip: Many people were dressed up at this spot but I was in ripped jeans and tennis shoes. The bouncer didn’t say anything and we were able to order drinks no problem. They had fire pits and quiet spaces outside which had a very different feel than the inside space which felt a bit like a club. It was a great view!


Day 2

After a full day, take it easy on your second day and start a little later. We stopped at a random diner during our bike ride along the way to our first stop.

Bike along the Lake

We had a Divvy Bike station right next to our AirBnB which made hopping on a bike super easy. Divvy Bike is Chicago’s bike share program. You can rent one of their bikes from any station around the city (there are tons!) and ride from spot to spot. A single ride is $2 or rent for the day for $15 so because we were planning to ride several times, we chose to rent for the whole day giving us freedom to bike everywhere we wanted to go.

I always try to fit in some sort of physical activity on a trip. Biking along the lake was not only gorgeous, but also gave us a chance to see the city from a different side. We stopped at 31st Street Beach for the view and continued on into the city to the Chicago Institute of Art.

If it wasn’t for the rain that weekend, we may have gone kayaking in Chicago on the river (it looks like so much fun!). Definitely something worth checking out if you go.

Chicago Institute of Art

I love museums and was very impressed with this one! It’s one of the top rated museums in the world with almost every type of art you can think of. Their impressionist collection was huge and I loved seeing all the Monet paintings the most. The flow is a little confusing but you’ll easily get around using a map.

We bought our tickets online which saved us a bunch of time. We were also carrying our bags around this day and baggage check was just $1 a bag so we decided to leave our bags there for the rest of the day. It was really easy and convenient.

Bike the Magnificent Mile

The Magnificent Mile is Chicago’s premier commercial district and is famous for all the shops and important buildings along Michigan Avenue running through downtown Chicago. The vibrant, bustling area is home to upscale shops and more. We were headed to a spot down the Magnificent Mile and with our full day bike rental, it made sense just to bike! It was fun to ride the bike lane through downtown though and get a closer look at all the shops as we rode past.

Cocktails at The Signature Lounge 

There are a few options of observation decks in Chicago like the glass floor at at the Chicago SkyDeck. I actually ended up seeing the Signature Room at Willis Tower on someone’s Instagram story and knew I had to visit! It’s free to enter this beautiful bar, but the price of a cocktail is the same as admission onto an observation deck.

The Signature Lounge is just two floors down (96th floor) from the observation deck above. We loved sitting and sipping our drinks though overlooking the entire city of Chicago though instead of wading through tourists. It was beautiful and the fact that a drink was included was worth it.

There’s also a restaurant located on the same floor of the building, but you will need a reservation to go!


Pro-tip: The Signature Lounge gets really crowded as the day goes on. We went around 2:30 and there was no wait. However, when we left at 4:00, there were at least 20 people waiting. Go early if you can.


Goose Island Brewery

It wouldn’t be a trip with my boyfriend if we didn’t stop at a brewery! We headed to Goose Island which was perfect because it was on the way to the airport and it was fun to check out a brewery we knew, but also get to taste their special brewery only beers. It was a Sunday afternoon and very chill with few people inside drinking so it was a relaxing stop for sure. We each were able to create our own flight and try a bunch of fun beers.

Fatso’s Last Stand

This was another hot dog spot (yes we ate hot dogs two days in a row – so what!) that came highly recommended and was pretty close to Goose Island and again, on the way out of town. The hot dogs were delicious and the mac and cheese was sooo creamy. Fatso’s is known for the cheese they add to their traditional Chicago dog and it was pretty delicious. It was a perfect last stop before heading to the airport.

Discover the perfect itinerary for spending two days in Chicago. Explore the city's stunning architecture, unique history, and vibrant food scene.
Discover the perfect itinerary for spending two days in Chicago. Explore the city’s stunning architecture, unique history, and vibrant food scene.

We loved Chicago, and I know you will, too! I hope this guide was able to help you as you plan how to spend two days in Chicago.

Meghan

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