2 Days in Chicago – A Weekend in Chicago Itinerary You’ll Love

Planning a weekend in Chicago, but unsure what to do to maximize your time?

We’ve put together a great itinerary for 2 days in Chicago that will showcase the full range of all that city has to offer in just a few days!

This weekend itinerary includes:

  • Hop-On Hop-Off Big Bus Sightseeing Tour
  • Skydeck Chicago
  • Art Institute of Chicago
  • Navy Pier (free!)
  • Museum of Science & Industry
  • Adler Planetarium
  • Field Museum
  • Shedd Aquarium

We’ve also put together a 1 day and 3 day itinerary.

Save on Attraction Admission

Pick up a 2-Day Go Chicago® Card and save off combined admission vs paying at the gate.

Remember, this 2 days in Chicago itinerary is just one of many ways to experience ‘The Windy City.’

The Go Chicago® Card gives you the flexibility to create your own itinerary, so you can choose from dozens of top attractions and create a vacation tailored to your interests.


Stop #1 – Hop-On Hop-Off Big Bus Sightseeing Tour


A Hop-On Hop-Off Chicago Bus Tour is the perfect way to get an overview of Chicago’s many landmarks and hotspots.

Since you probably won’t get the chance to see everything on your 2 days in Chicago, this will give you the opportunity to at least learn a little about all the major landmarks.

Some of the highlights you’ll see include all the big names in Chicago tourism: the Willis Tower, Navy Pier, the Museum Campus, the Water Tower Mall, and many more.

Getting In: Hop-On Hop-Off Chicago Bus Tour tickets are included on the Go Chicago Card.

Stop #2 – Skydeck Chicago


Be sure to head to one of Chicago’s most recognizable buildings, and a quintessential tourist “must do,” Skydeck Chicago in the Willis Tower. Skydeck Chicago provides some of the best views of the city, from 1,353 feet up in the air!

This is a great photo opportunity. You’ll see the downtown skyline, Millennium Park, Soldier Field, Navy Pier, and the entire sweeping coast of Lake Michigan.

Tip: visit in the morning for beautiful morning views of the city, as a bonus, you’ll avoid long lines by doing this first thing in the morning.

All visitors are required to go through a security line, which will add some time onto your visit. We recommend reserving about an hour and a half for this attraction, including wait time in the morning.

Getting In: SkyDeck Chicago at Willis Tower tickets are included on the Go Chicago Card.

Lunch at Navy Pier

Hop off the bus at this popular destination, setting yourself up for both of your next attraction visits and for lunch.

You’ll find so many dining options here that it will be hard to choose, but you can’t go wrong with a Chicago style hotdog. There are even some great desert options, like the Haagen Dazs Café.

Stop #3 – Option 1 (indoor): Art Institute of Chicago


If something wins #1 Museum in the World in a Trip Advisor poll, you know it’s a must-visit. The Art Institute of Chicago should definitely be on your weekend in Chicago itinerary, whether you’re a huge art lover or just someone who appreciates pretty things.

The Art Institute boasts renowned collections of art and artifacts that include everything from Roman and Greek sculptures to modern and contemporary painting. Some of their most popular pieces are drawn from an impressive collection of Impressionist painting and their extensive George O’Keeffe holdings.

You’ll also get to see some famous pieces that we’re sure you’ll recognize, like the Chagall stained glass windows, Grant Wood’s “American Gothic,” and Henri Matisse’s “Bathers by a River.” A visit here is definitely inspirational. 

Getting In: Art Institute of Chicago tickets are included with the Go Chicago® Card.

Stop #3 – Option 2 (outdoor): Architecture River Cruise


You can pick up this cruise right nearby Navy Pier. The Architecture River Cruise is one of the most informative tours you’ll ever take, and it provides a unique perspective on Chicago’s glorious architecture.

Learn all about the history of Chicago’s skyline as you glide down both branches of the Chicago River. From the Great Chicago Fire of 1871 through various artistic movements to the modern architectural boom, Chicago’s skyline has undergone a number of architectural shifts that make for a fascinating, eclectic skyline.

This cruise lasts 75 minutes; we recommend arriving at least 15 minutes in advance of your desired sail time.

Getting In: Chicago Architecture Boat Tour tickets are included on the Go Chicago Card.

Stop #4 – Navy Pier

Navy-Pier-centennial-wheel-1Once you’ve completed your cruise, you’re right back at the world famous Navy Pier.

It’s Chicago’s most popular free attraction for a reason! Wander around and just enjoy the environment, or opt to visit any of the exciting museums, theaters, and other attractions.

One family favorite option is the Navy Pier Centennial Observation Wheel, which is included with your Go Chicago® Card. There are also other amusement park style rides, like swings and mini-golf!

Admission to the pier itself is free, although additional attraction visits may incur admission fees.

Getting In: Navy Pier Centennial Wheel tickets are included on the Go Chicago Card.

Dinner in the Loop

Located just west and south of Navy Pier, this neighborhood is filled with tons of restaurant options that span the gamut in terms of genre, price, and vibe.

Whether you’re looking for some cheesy and delicious deep-dish pizza or some high-grade sushi fusion, you’ll find it in this neighborhood.

For something a bit more casual, Sweetwater Tavern is a favorite among locals for a good beer selection and a fun bar menu.

After dinner, don’t forget to leave a little time to explore Millennium Park. It’s a lush urban greenspace in the heart of Chicago that locals love to gather in, day or night.

Filled with art installations like Cloud Gate (aka, the Bean) and famous architecture like the Pritzker Pavilion, it’s a great free attraction for when you’ve got some time to roam.


Stop #1 – Museum of Science & Industry


Start your second day off with a visit to one of country’s most exciting science museums (and the largest!).

The Chicago Museum of Science and Industry is filled with interactive and informative exhibits that will delight children of all ages.

Did you know that this museum is actually housed in the only remaining building from the 1893’s World’s Fair? Some of their fascinating offerings include a genuine WWII German submarine, a recreated coal mine, an eco-friendly home, and more!

Proceed directly to the Will Call desk for entry. We recommend spending about an hour at this attraction.

Getting In: Museum of Science & Industry tickets are included on the Go Chicago Card.

Stop #2 – Adler Planetarium


Explore 91 billion light years of all things related to the Universe at the oldest planetarium in America, the Adler Planetarium.

A visit here is a great way to immerse yourself in the “magic and wonder of space.” Explore their several different exhibits, take in a show, and experience the historic Atwood Sphere.

The museum’s exhibits are all highly educational and entertaining; familiarize yourself with Earth’s cosmic backyard with a fast-paced tour in Destination Solar System, catch one of the planetarium’s popular shows like Planet Nine or Skywatch Live, kids especially will love getting to climb and fly through the Planet Explorers exhibit, and more.

Enter through the South Box Office for admission. We recommend reserving between 1-2 hours at this attraction.

Getting In: Adler Planetarium tickets are included on the Go Chicago Card.

Lunch on the Museum Campus

Since you’re right here, it’s easiest to plop down for lunch on the Museum Campus itself. You have several restaurants to choose from, including cafés and dining halls in each of the three institutions.

Some local favorites include:

  • Café Galileo’s: located right in the Adler Planetarium, this museum restaurant features sandwiches and salads with skyline views
  • Del Campo’s Tacos: located just south of Adler Planetarium, this popular taco joint offers casual outdoor dining and waterfront views
  • Kim & Carlo’s Chicago Style Hot Dog Cart: located right outside The Field Museum, this is a tourist experience in itself where you can check “eat a Chicago-style hot dog” off your Chicago ‘Must-Do’ list
  • Giordano’s: located a little west of Museum Campus, this is one of the best places in Chicago, according to locals, to grab deep-dish pizza

Tip: don’t forget to take in the beautiful views from the Museum Campus – the best view of the Chicago skyline is between Adler and the Shedd Aquarium.

Stop #3 – The Field Museum


One of the premier natural history museums in the world, The Field Museum has something to offer everyone.

Featuring objects and artifacts from literally billions of years of history, this museum is a one-of-a-kind institution in Chicago that will particularly appeal to history buffs.

Meet “Sue,” the museum’s famous T-Rex skeleton (one of the most complete skeletons of its type), marvel at their gorgeous collection of gemstones, explore collections of Ancient Egyptian artifacts, and wander through the “Underground Adventure” exhibit.

Proceed to the South Will Call entrance for admission. We recommend budgeting between 1-2 hours for this attraction.

Getting In: The Field Museum tickets are included on the Go Chicago Card.

Stop #4 – Shedd Aquarium


The Shedd Aquarium is every kid’s favorite Chicago destination. Filled with wondrous creatures, great and small, this iconic institution is the perfect place to indulge the animal lover in all of us.

Home to more than an astounding 32,000 specimens from marine habitats around the globe, Shedd has more than 1,500 different types of creatures on display. From sharks and sea otters to jellies and tropical fish, you’ll find all your favorites here!

Proceed to the Will Call line for admission. We recommend reserving between 2-3 hours to explore this attraction.

Getting In: Shedd Aquarium tickets are included on the Go Chicago Card.

Dinner in Little Italy

A neighborhood located just west of the Museum Campus, this area is a great destination for authentic Italian food and Chicago-style pizza.

You’ll find other cuisines, of course, (especially pub-style fare), but we recommend the pizza!

Let’s Recap

So there’s your perfect 2 days in Chicago weekend itinerary!

From museums to bus tours to boardwalks and cruises, you’ll leave the Windy City feeling like you’ve literally seen all there is to see.

Pick up a 2-Day Go Chicago® Card and save big off admission prices when you these visit included attractions.

Go Chicago Card

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