2 Day Chicago Itinerary: A Weekend in the Windy City

If you are planning a trip to the Windy City, this 2 day Chicago itinerary includes all the highlights. Plan as much time in the city as you can though — there is truly so much to see and enjoy here!

When we went to Chicago, I honestly did not expect to love it as much as I did. Really, the main reason we went was to see Hamilton (which is sadly no longer playing in Chicago), and seeing the city was more of an afterthought. I think I had some kind of stereotype of Chicago in my head and didn’t expect much. But we discovered a friendly, beautiful city that we really fell in love with!

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How to Get to Chicago

The obvious way to get to Chicago is to fly. Both O’Hare and Midway airports have Chicago Transit Authority (CTA) trains that connect directly to the center of the city. From O’Hare you’ll take the Blue Line, and from Midway you can take the Orange Line.

Taxis and Ubers/Lyfts are also an option to get to downtown from the airport. (This is what we did when we flew out because our flight left so early in the morning.)

Since Chicago is an Amtrack hub, you could also choose to take a train to Chicago if this is convenient for you. Trains arrive at Union Station in downtown Chicago.

You can, of course, drive to Chicago, although keep in mind that this is a large and densely populated city, so be sure you have a plan for where you will park your car.

2 Day Chicago Itinerary

Day 1

For day one we’ll mostly focus on Chicago views — exploring the beautiful parks and the architecture of the city.

Waterfront Parks

Start your first morning in Chicago exploring the waterfront parks. Sometimes, when I’m in a new city I like to ground myself with some beautiful views and wide-open spaces (as opposed to a jumble of buildings) and that’s exactly what you’ll get here.

Head to Millennium Park and check out Cloud Gate (aka The Bean). The wander the paths here and see the Crown Fountain.

You can also cross the street to Maggie Daley Park (where there is an ice skating rink in the winter!). And be sure to continue south to see Buckingham Fountain.

To enjoy a bit of Lake Michigan, cross Lakeshore Drive and enjoy Lakefront Trail.

Really just enjoy all this green space in Chicago as much as possible — it’s really a beautiful part of the city!

Art Institute of Chicago

After spending some time outside grab lunch and then head to the Art Institute of Chicago, one of the city’s most renowned museums. It’s located right next to Millennium Park, so it’s easy to get to from your morning of exploring.

Here you’ll find art from all around the world, including some of the most famed works in all of art history. The Art Institute of Chicago also houses the Thorne Miniature Rooms, a series of 68 intricately designed dollhouse-size rooms.

You will need to buy tickets for the Art Institute of Chicago ahead of time. If you’ll be visiting a lot of museums on your visit, you might consider looking at the attractions covered by the Go Chicago Pass.

Also be sure to check museum hours before your arrival, as they are always subject to change, but they usually open mid-morning.

River Walk

After some time at the museum, head to the Chicago Riverwalk. This iconic area is a great place to stroll along and/or people watch — it’s so fun to watch all the boats go by!

Plus this is exactly where you need to be for our next stop!

Architectural Boat Tour

For the late afternoon, take a boat tour of Chicago. You’ll see a lot of different places offering “tours” but the true tour and the BEST one to get is the Architectural Boat Tour through the Chicago Architecture Foundation.

This was one of my favorite things we did in Chicago — honestly a surprise hit. The tour will take you up and down the Chicago River and your docent will explain Chicago’s architectural history, building challenges, urban planning stories, and historical events.

I know this may not sound like the most exciting thing, but I promise you it is amazing! You will learn so much, plus it is a GREAT way to see some of the most iconic buildings in Chicago. And it’s just a pleasant boat ride!

Definitely reserve your tour spot ahead of time!

See the Views from Above

After dinner, it’s time to see Chicago from the top of one of it’s iconic buildings. There are several viewing areas in Chicago, including 360 Chicago and Skydeck Chicago. Both of these charge admission fees and often have long wait times.

So my favorite is to see the views from The Signature Lounge at 95th located in the John Hancock Building (the same building that houses 360 Chicago). This is a bar attached to a restaurant (The Signature Room at 95th) where you can grab a drink and enjoy the views. One tip — front row window seats are given out by servers on a first come first serve basis, so let your server know you’d like one and they can move you up when one becomes available.

Another tip: the women’s restroom here has the BEST views!

Of course, if you’re traveling with kids, going to a bar for city views is probably not your ideal option. In that case, definitely look into one of the ticketed viewing locations. They are open pretty late into the evening, so you can still save this for later in the day. Plus, sunset and nighttime views of Chicago are beautiful!

Day 2

For day two of our 2 day Chicago itinerary, we’ll his some museums, see Wrigley Field, and hang out at Navy Pier. These sights are a bit more spread out than our day one sights. So have a plan for transportation, whether you want to take a taxi or Uber/Lyft or want to take the train around.

Head to a Museum

Start your second morning out with visiting one of Chicago’s renowned museums. Some of most popular options include the Field Museum (which features history and science) or the Shedd Aquarium.

Be sure to check hours and admission prices before you go. And we always recommend buying tickets ahead of time. (Also, if you plan on hitting up a lot of museums, the Chicago Go card might be a good investment for you. But be sure to look at how the price of the card compares to the cumulative price of all you plan to visit.)

The Magnificent Mile

After lunch, head to Chicago’s most famed shopping street: The Magnificent Mile. Really this is North Michigan Avenue, but it has garnered the nickname of The Magnificent Mile for being the premier retail and commercial area of Chicago. Here, you’ll find stores for favorite brands, plus some Chicago landmark buildings.

Even if you aren’t a big shopper, you can take some time to walk through the area and window shop (and people watch! are we seeing a theme there? this is apparently one of my favorite travel activities.).

Wrigley Field

It seems silly to come to Chicago without going to see Wrigley Field, so head there for the afternoon. If you are really into baseball (and there’s not a baseball game going on that day), you can schedule a tour.

Otherwise, just take some time to walk around the stadium. It’s a truly unique place that is the heart of the neighborhood — instead of being surrounded by tons of retail space it’s surrounded by homes with rooftop decks for watching games. You can of course stop into the gift shop too for a fun souvenir.

Bonus Book Stop: Women and Children First

When you’re at Wrigley Field you won’t be too terribly far away from one of Chicago’s independent bookstores: Women and Children First. It’s about a 10 minute drive away.

Stopping by a city’s independent bookstore is one of my favorite things to do when traveling, and I always try to bring a book home that reflects where I’ve been. They have great books to choose from and can help you find books by local Chicago authors (or anything else you want to read).

I loved visiting Women and Children First, but if you want to find another indie bookstore closer to some of your other stops, you can always use Indie Bound’s Indie Bookstore Finder, which is also a great tool to keep in your pocket for any other trips.

Navy Pier

For the evening, head to Chicago’s Navy Pier. This is one of the most popular tourist areas of the city, but with good reason. It has a fun, carnival-like atmosphere with lots of family-friendly activities. There are restaurants, a ferris wheel, rides, and even a greenhouse garden.

Some select nights during the summer they also have fireworks (so check the schedule and maybe rearrange your evening activities if seeing fireworks is important to you.)

Depending on what you want to do at Navy Pier, you may need to buy a ticket. For example, for the rides you’ll need a ticket for Pier Park Attractions. See more here about Navy Pier tickets.

Where to Eat in Chicago

Chicago has so many great places to eat, and unfortunately there’s no way to get to all of them in a 2 day Chicago itinerary. Here are a few we loved on our trip though, plus some others we wanted to try and will be on our list next time.

Little Goat — We had a GREAT breakfast here!
Beatrix
Quartino — We loved everything we had at this Italian restaurant.
Avec
Au Cheval — They supposedly have the best burgers here (and this is my first priority to try next time we’re in Chicago!)
Giordano’s — There is a great debate about what restaurant has the best deep dish pizza, but several locals told us this was the place to try, so we did! And there’s several locations throughout the city.

Tips for Traveling to Chicago

Wear comfortable shoes. Chicago is super walkable and you’ll be walking a lot, so make sure you wear good shoes!
Visit in the summer. Summer is one of the best times to be in Chicago! The weather is pleasant and the days are long enough so that you can see and do a lot! Winter will be too cold to be able to see or do much. If you don’t want to do summer (which can be pricier because it’s high tourist season), spring and fall are also great times to visit Chicago — in the spring once it warms up a bit and in the fall before it gets too cold.
Bring a jacket. Even in the summer, Chicago may require a light jacket, especially in the evenings.
Buy tickets for your attractions ahead of time and/or look at the possibility of getting a Go Chicago Pass.

There is no way a 2 day Chicago itinerary is long enough — after our two day trip to Chicago, I definitely want to go back again and see more! But if you have just a weekend to travel to the Windy City, this itinerary will help you see all the best the city has to offer!