How to Spend a Weekend in Chicago: The Perfect 2-Day Itinerary
Disclaimer: This post contains affiliate links, which means I may earn a commission if you make a purchase through these links, at no extra cost to you.
Looking for a fun weekend city escape? This two-day Chicago itinerary covers all the highlights—from iconic architecture and museums to deep-dish pizza and lake views—for the perfect weekend in Chicago.
Chicago also has a great public transportation system and many of the best attractions are easy to get to. There is also some really great food and vibrant nightlife. This itinerary will help you hit the best of Chicago on a short weekend trip.
Day 1: Exploring Chicago’s Iconic Sites
Morning: Sightseeing and Millenium Park
Hop on a train or take a walk from your hotel over to Wildberry Pancakes and Cafe for breakfast, soaking in the sights of the city while you walk. This is one of my favorite breakfasts in the Chicago area and I make sure to try to plan a stop here every time I’m in the area. I personally love the Signature Berry Bliss Crepes but everything I’ve tried here has been great.
Wildberry is right next to Millenium Park so after breakfast head to the park and take your picture with “the bean” which is actually a piece of art called Cloud Gate. Walk through the park and along the lakefront area as you make your way towards the museums.
Late Morning/Afternoon: Museums
You won’t be able to visit all of the museums in this area in one short weekend trip unless visiting the museums is the only thing you want to do so for this itinerary we’ll just choose one museum. The museum campus area has three options: the Field Museum, Shedd Aquarium, and Adler Planetarium.
Choose the Field Museum if you prefer history or want to see the giant dinosaur fossils. Choose Shedd Aquarium if you’re more interested in fish, penguins, and sea otters. Adler Planetarium is great for educational value but I feel like it is the weakest of the three museums here. If you are particularly interested in seeing the planetarium, this could be the choice for you but if you’re only somewhat interested, I would choose the Field Museum or Shedd Aquarium.
Spend some time at the museum of your choice and then walk along Lake Michigan back towards the center of the city.
Evening: Navy Pier or Dinner and a Show
As you’re walking back along the lake, you may want to visit the iconic Navy Pier if you’re visiting in the warmer months. This classic Chicago attraction has a variety of activities including rides, games, food, shopping, and cruises on the lake.
An alternative option would be to get some classic Chicago deep-dish pizza for dinner from either Lou Malnati’s or Giordano’s. Everyone in Chicago has very strong opinions about which one is better so it really comes down to personal preference. If it’s your first visit, it’s okay to just choose one and go with it. My favorite is Lou Malnati’s.
Then, after your dinner, you could see a Broadway show, a comedy show, or find some live music. There is always a wide variety of performances and shows happening around the city on any given night so choose one that speaks to you.
Day 2: Sightseeing, Shopping, and Culture
Morning: Sightseeing
The morning of the second day is a great time to wrap up any other touristy sightseeing things you may want to do. I suggest doing these in the morning before they get too busy. My recommendation would be to do a city view activity such as Skydeck Chicago. You’ll get the chance to see Chicago from one of the city’s tallest buildings and step out on the glass bottom ledge.
Another good option would be to do one of the famous architecture river cruises. These run throughout the day but if visiting in the summer it might be nice to do it before it gets too hot. It’s a great way to see more of the city and learn about the architecture of the buildings.
Afternoon: Art Museums or Shopping
Most of the art museums open a little bit later in the morning so the afternoon is a great time to visit. The Art Institute of Chicago, the Chicago Cultural Center, and the Museum of Contemporary Art are all excellent choices. This is a great option for anyone who can appreciate artwork.
Chicago is also known for the Magnificent Mile – a famous shopping area. If art museums aren’t your thing or you’re looking to spend an afternoon shopping, this is a super fun area to explore. You’ll get the chance to see some of the most iconic buildings in Chicago as you walk around and do some shopping. Starbucks lovers may also want to stop by the Starbucks Reserve Roastery.
Evening: Dinner and Drinks
Chicago has some great nightlife options. For the last night of the trip, let’s look for something a little bit more laid back – grab some dinner, and then get drinks at a rooftop bar. Alternatively, you could do a sunset cruise on Lake Michigan or the river.
Tips for Your Weekend in Chicago
How to Get Around
Chicago has an excellent public transportation system. Buses and trains run all over the city and are incredibly easy to use. The trains also go to the airport, making it easy to get from the airport to the city center.
Best Times to Visit Chicago
Chicago has plenty going on year-round. I would argue that winter can be a difficult time to visit because of the cold and potential snow. However, before Christmas time there are some fun and interesting activities such as ice skating at the Maggie Daley Park Ice Skating Ribbon or going to the Christkindlmarket Chicago.
In spring, the temperatures can still be pretty chilly, especially with the wind – they call it the Windy City for a reason! However, St. Patrick’s Day can be an interesting time to visit with the river dyed green. Be prepared for a pretty rowdy crowd as most people will be spending St. Patrick’s Day at the bars in the city.
Summer can be hot but I think it’s my favorite time to visit Chicago. The warm weather makes the boat activities more pleasant and it feels like the perfect time to visit Navy Pier. Early fall before the temperatures drop too much can have a similar feel.
Fall can be pretty with the leaves changing colors and offers an excellent time to visit if you’d like to explore in cooler weather. Just again, be prepared for the wind to make things a little bit chillier.
Planning a trip to Chicago? Let me know what you’re looking forward to the most in the comments!
Need help planning your trip? See my post on how to plan the perfect weekend getaway or sign up for my newsletter below and get a free Weekend Getaway Planner to help you keep track of all of the details!
