Chicago in 2 Days – See the Best Sites – Free Itinerary

Traveling to Chicago, but only have a weekend in the Windy City? You’ve come to the right place! Here it is! The ultimate guide to Chicago in 2 Days! See the best sites of Chicago in 2 days and feel like you did it all even in a short amount of time! I’ve created a FREE downloadable Itinerary as well as a link to a map with all these spots pinned!

Free Downloadable Itinerary and Access to my Google Maps Pins at the bottom of this post!

This itinerary is meant for 2 full days. I recommend flying in a little early or fly out late to have at least a half a day extra to do anything else you may have missed. For details of Things to do in Chicago see this post. For the Best Chicago City Views information and locations, see this post.

To and From the Airport

The first thing to have to consider is how you will get to and from the airport. Most people fly into Chicago O’hare and this is where I flew into. Don’t take an Uber or Lyft, trust me, its expensive and traffic can get crazy giving you less time in the city. Take the Chicago Transit Authority (CTA) L Train blue line all the way into the city. It takes about an hour to get to the heart of the city, but it is much cheaper than a taxi or Uber and you will not get stuck in traffic. The process is very simple and you can purchase your transit tickets in the airport before boarding.

Getting Around

You will also want to take the L train to get around the city, especially places that are not walking distance. Uber and Lyft are options but they can be pricey and pick up points can be tricky. The Chicago transit system is great and affordable. I recommend purchasing the 3-Day CTA Pass for only $15 which will give you unlimited rides during those days and get you to and from the airport! For the latest Fare information and visit the Chicago Transit Authority website.

Where to Stay

There are numerous hotel options to stay in Chicago. I recommend the River North area. Yes it’s touristy, but it’s walking distance to most of the where you’ll be visiting anyway, and it is close to the L Train transit system. Any hotels in Magnificent Mile will put you walking distance to restaurants and tons of shopping. I have stayed at the Chicago Marriott Downtown Magnificent Mile and it was a great hotel with a convenient location!

If you want a Lake view, look for hotels closer to Navy Pier. If you want more of a river view, find a hotel close to or on the river, and the taller the hotel is the more likely you’ll get a view (but you will have to book or request a river view hotel that may cost more money or not be available). I stayed at the Renaissance Chicago Downtown Hotel and would 100% stay here again! Since I’m a Marriott girly and have status I was able to use my “Suite Nights” rewards for an upgraded river view suite and it was absolutely stunning! But even without an upgrade this is great hotel conveniently located by the river, the Chicago Theater, and transit lines.

Okay let’s get into this itinerary!

Day 1

Morning

We’re going to knock out the majority of the absolute must do touristy activities on this day to make sure they get done!

Start early in the morning at The Bean for the least amount of crowds and to get some great photos!

Next you’ll explore Millenium Park and surrounding areas. Check out the Crown Fountain, an interactive fountain and splash pad area. Go to Maggie Daley Park for the most amazing jungle gym and slides with a great city backdrop. This is a GREAT place to take kids but even as adults, my husband and I enjoyed walking through the park (and yes going down the slides lol). You can also trek over to Buckingham Fountain, another well known Chicago site.

Take a break and eat some Brunch around this area. Although it is catered to tourists, there are a lot of great spots to eat. In my Itinerary I have some recommendations on where to eat. In addition to these options, if you are wanting some adult beverages, check out Cindy’s Rooftop, or The Berghoff. Also the “Goth” Target is in this area, which is just a regular Target inside a Gothic Style building.

After refueling, head to the Art Institute of Chicago (the earlier the better for less crowds). This is an AMAZING art museum and one of the largest and oldest in the world. It’s a major tourist attraction and was featured in Ferris Bueller’s Day Off movie. You will be in here for hours.

Evening

From here, head back to your hotel and rest/change (if you have a million outfits like me). Or you could head to Magnificent Mile, walk around, shop and see the sites. Stop by the Starbucks Reserve and Roastery for some caffeine and explore the largest Starbucks in the world!

Now you’ll go on an Architecture Boat Tour to learn all about the city’s history and architecture as well as sight see. Although this is the most pricey of the activities I recommend, I highly recommend this experience!

After that have some dinner, and sight see some more or enjoy Chicago’s nightlife. The Itinerary has some recommendations in the River North area. If it’s nightlife you’re looking for, check out this post Best Bars and Speakeasies of Chicago.

Day 2

Morning

Start your morning off with amazing views of Chicago from up above at the tallest building in Chicago, Willis Tower. Sky Deck Chicago is a great experience for all ages that I highly recommend. Not only are their views amazing, but the interactive experience while walking through the line is the cherry on top! Going early will help you avoid large crowds, and there will be less of wait for experiences like The Ledge (a glass balcony 1,353 feet in the air).

Next you can head to West Loop (less touristy, more local), or River North for some lunch. West Loop is a neighborhood that I love in Chicago and I typically recommend going here if you have a little more time in the city, and especially for night life with a little more of a local feel. River North is catered to tourists but has all the Chicago staples including Chicago dogs from Portillo’s, or numerous options for some Chicago Deep Dish pizza! I’d say River North is better for families with kids, West Loop is more for the adults.

Evening

Next you’ll explore River North. There are recommendations on the Itinerary, but you can walk the River Walk, take the kids to Navy Pier, walk and shop Magnificent Mile, take in views at a rooftop bar along the river, really anything you are feeling.

On your trip I highly recommend going to a Cubs game at Wrigley Field! Learn all about Wrigley Field in my Baseball Stadiums Post! If it’s not Baseball season or that’s not your thing, go to either a Comedy Show (Chicago is famous for comedy), or a Broadway Show (I watched Hamilton in Chicago).

You are then going to grab dinner before your show, or head to Wrigleyville and enjoy exploring near the stadium for some food and pre-gamming.

After that, you can go back and rest up for your flight in the morning, hit some spots you didn’t get to see, or enjoy the night life!

Chicago in 2 Days

This Itinerary allows flexibility in what you want to do, since every person and family is different. I hope it helps you to plan your trip to Chicago and gives you some good suggestions. Please let me know in the comments or email me to let me know if this Itinerary, Map and post helped you!

Access the FREE Chicago 2-Day Itinerary by clicking above!

Click above to access the Link to my google map of pins for Chicago!

I hope this post helps you plan your trip to Chicago Illinois! Let me know what you think in the comments!