Chicago Itinerary – 3 Days in Chicago for First Timers

Chicago is a city that tourists simply can’t get enough of. However, it comes as no surprise as this city offers diverse cultural experiences. You can experience world-class museums, exciting culinary adventures, and renowned architecture. Plus, some of the nation’s favorite attractions.

Most Chicago visitors don’t have enough time to do everything in one trip. It can be difficult to decide what to do and when to do it. Additionally, there is always something new in Chicago to see or do.

However, we just made your trip a lot easier with our 3 Days in Chicago Itinerary.

From arts and culture to science and entertainment, you’ll find a little bit of everything on this Chicago itinerary.

As Chicago weather varies so dramatically between seasons, we’ve also included some indoor and outdoor options. Therefore, you can make this itinerary work for a vacation any time of year.

This 3 day itinerary includes:

  • Check out our helpful Chicago itinerary infographic here.
  • Big Bus Chicago Hop-On Hop-Off Bus Tour
  • Shedd Aquarium
  • The Field Museum
  • Adler Planetarium
  • Chicago Theatre Tour OR Architecture River Cruise
  • 360 CHICAGO
  • Magnificent Mile (free!)
  • Chicago Children’s Museum OR Bike Rentals
  • Navy Pier Centennial Wheel & Rides
  • SkyDeck Chicago
  • The Art Institute of Chicago
  • Millennium Park (free!)

Only have a few days in Chicago? We’ve also put together a 1 day and weekend in Chicago itinerary.

Save on Attraction Admission

Pick up a 3-Day Go Chicago® Card and save off combined admission vs paying at the gate.

Remember, this 3 day itinerary is just one of many ways to experience Chicago.

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 Chicago Tour


big bus Chicago hop on hop off

This attraction is your perfect introduction to the Windy City. Your Chicago Hop-On Hop-Off Big Bus Tour will take you past all the top attractions and landmarks, and your knowledgeable and friendly tour guides will fill you in on all the important facts and insider info.

It’s a great way to get oriented within the city as a whole before you start exploring on your own. A few of the highlights of your tour include the Museum Campus, Navy Pier, Water Tower Place Mall, Willis Tower (formerly Sears Tower), and more.

You’ll be able to disembark at most landmarks, so it’s easy to use this your to further your itinerary (although traffic can be a factor, so don’t rely exclusively on your Hop-On Hop-Off bus for transportation). Or, as the tour lasts 2 hours, you could stay on the bus for the whole route to see as much of the city as possible.

Remember to pick up your ticket in advance of boarding from the Big Bus admission desk. Simply show your Go Chicago pass.

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

Stop #2: Shedd Aquarium

Shedd-Aquarium-Discount-3Next, head down to Chicago’s Museum Campus and pay a visit to its crown jewel – the Shedd Aquarium. Home to 32,000 fascinating and unique creatures from a range of diverse habitats, Shedd is one of the best (if not the best) aquariums in the country.

Popular exhibits included with your admission are “Waters of the World,” “Caribbean Reef,” “Amazon Rising,” “Abbott Oceanarium,” “Wild Reef,” and the “Polar Play Zone.” Plus, be sure to check out their new attraction, “Underwater Beauty.”

Shedd Aquarium also allows you to get up close with the animals – you can feel stingrays at “Stingray Touch” at no additional cost. However, if you want a truly memorable experience, you can meet a beluga whale, a sea otter, or a penguin, for an additional fee. Check out the Shedd Aquarium’s Extraordinary Experiences for more information.

Proceed to Will Call for admission. In the summer months, this can save you significant time that you would have lost standing in line. What a win!

We recommend reserving at least 2-3 hours for this attraction – there’s so much to see and do.

Getting In: Shedd Aquarium tickets are included on the Go Chicago Card. Please note that Shedd Aquarium’s Extraordinary Experiences are not included in the Go Chicago admission.

Stop #3: The Field Museum

Chicago field museum

After lunch, head to this popular natural history museum for an educational and entertaining afternoon.

The Field Museum has spent over 100 years curating and adding to its collections, so you know their selection and breadth of artifacts and objects will be impressive.

Some of the highlights of their collection include SUE, the famous T-Rex (the most complete skeleton of her species), the notorious Tsavo Lions, an extensive collection of Ancient Egyptian artifacts, a beautiful selection of gemstones and minerals, and the fun “Underground Adventure” exhibit.

We recommend reserving between 1-2 hours for this attraction.

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

Stop #4: Adler Planetarium

Adler-Planetarium-3End your day with a visit to the last (but by no means the least) of the Museum Campus institutions. The Adler Planetarium has a lot to offer curious visitors.

With nine special exhibits, multiple theaters, and the historic Atwood Sphere experience, there are tons of fun activities that the whole family will enjoy.

Popular exhibits include “Planet Explorers,” “Shoot for the Moon,” “Astronomy in Culture,” Hidden Wonders,” and more.

This is a must-see attraction for any aspiring scientists or space-lovers in the family.

We recommend reserving about 1 hour for this attraction.

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


Stop #1: Chicago Theatre Tour (Indoor Option)

The-Chicago-Theatre-1Take an amazing tour of the iconic Chicago Theatre, home to legendary performances by world-class actors. One of the most well-regarded historic theaters in the country, this venue is a must-visit for history buffs and culture lovers.

On this tour, you’ll get to walk across a stage that’s played host to the likes of Frank Sinatra and Dean Martin. Plus, you’ll see the walls with tons of celebrity autographs scrawled across them.

Of course, don’t forget about the gorgeous French Baroque interiors! This venue is a beauty from top to bottom. 

Getting In: Chicago Theatre Tour tickets are included with the Go Chicago Card.

Stop #1: Architecture River Cruise (Outdoor Option)

chicago architecture river cruise go city

Photo by Chicago Architecture Foundation

Start off your morning with a beautiful cruise down the Chicago River. This cruise only runs during the warmer months (and can be a bit too chilly during the early spring and late fall, even if it is running), so we recommend reserving this attraction for the warmest times of year.

This informative and insightful cruise will provide you with background information on Chicago’s most iconic landmarks and its famous skyline, practically building by building.

Some of the highlights you’ll see you on your Architecture River Cruise include buildings by Mies van der Rohe, Skidmore Owings Merrill, and Helmut Jahn, plus the Willis Tower and the Old Post Office Building.

It’s a must not only for fans of architecture, but for anyone who really wants to get a feel for Chicago’s history, particularly the history of the built environment after the Great Chicago Fire of 1871.

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

Stop #2: 360 CHICAGO

360 Chicago go city pass

Image Credit: 360 CHICAGO

360 CHICAGO is the newly renovated observation deck of the iconic John Hancock Tower, located on Michigan Avenue.

A visit here is both a great photo opportunity and a good chance to learn more about Chicago’s famous architecture.

From your 94th floor vantage point (over 1000 feet in the air!), you’ll get unparalleled, 360-degree views of the Lake Michigan and the city below. Don’t forget to look out for the Navy Pier Centennial Wheel!

As a bonus, this attraction is very conveniently located in the heart of an area you’ll definitely want to explore anyway — Michigan Avenue!

We recommend reserving at least 1 hour for this attraction.

Getting In: 360 CHICAGO tickets are included on the Go Chicago Card.

Magnificent Mile (free!)

Once you leave 360 CHICAGO, wander along Michigan Avenue (a.k.a. the Magnificent Mile) in search of some more fun.

There’s a boatload of shopping around,  including everything from affordable fashion to high-end boutiques that are just perfect for window-shopping. There’s also loads of dining choices, so you’re sure to find something to enjoy during even a quick stroll down Michigan.

You’ll find plenty of options, especially if you explore side streets. The nearby Water Tower Place Mall has a food court, too, which offers a selection of options that even the pickiest eater will find delicious.

Stop #3: Chicago Children’s Museum (Indoor Option)



Located right on Navy Pier, the Chicago Children’s Museum is a family favorite. Full of interactive exhibits, dynamic displays, and educational fun, there’s so much to do at this institution that your kids will never tire of it.

Featured exhibits and areas include “Dinosaur Expedition,” where kids can explore a real excavation pit where dinosaur fossils were discovered, and “Tinkering Lab,” which allows kids to exercise their creativity and analytical skills by playing around with different parts and tools. 

Getting In: Chicago Children’s Museum tickets are included with the Go Chicago Card.

Stop #3: Bike Rental (Outdoor Option)

Bike-and-Roll-Rentals-And-Tours-2After lunch, head down to the Navy Pier area to get little exercise. Rent a bike and enjoy the waterfront on two wheels! Chicago is a cyclist’s paradise, filled with trails, parks, and pathways just waiting to be explored.

There are actually 26 full miles of lakefront trails for you to enjoy, so you’ll really be able to get a feel for the beautiful scenery (and get one heck of a workout!).

Your rental is valid for 4 hours, but if you want to see an additional attraction today we recommend reserving only 2 hours for this attraction.

Getting In: Bike and Roll Chicago rentals at Navy Pier are included on the Go Chicago Card.

Stop #4: Navy Pier Centennial Wheel

Navy-Pier-centennial-wheel-1 Chicago go cityWhether you’ve tootled around on a bike or explored the Children’s Museum, be sure to also reserve some time to explore the Pier itself. It’s Chicago’s most-visited free attraction and has tons to offer the out-of-town visitor.

With attractions as varied as the Chicago Children’s Museum and the Chicago Shakespeare Theater to a massive concert venue, you can practically spend the entire day here!

One of the most popular attractions on Navy Pier is its iconic Ferris wheel, visible from many vantage points across the city.

There are also a few other theme park-style rides to enjoy, from swings to a mini-golf course.

Although entrance to the Pier itself is free, your Go Chicago pass covers the admission costs for the Centennial Wheel and other rides. We recommend reserving 1 hour for this attraction.

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


Stop #1: SkyDeck Chicago

skydeck chicago go cityCheck out Chicago’s other sky-high attraction – SkyDeck Chicago at the Willis Tower. From the 103rd floor of the tower you’ll be treated to stunning and unbeatable views –1,353 feet up in the air!

Some of the highlights you’ll be able to see in the city below include everything from Navy Pier to Soldier Field and the Museum Campus. Don’t forget to bring your camera to this attraction!

We recommend reserving 1 hour for this attraction.

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

Stop #2: The Art Institute of Chicago

Chicago art museum go cityNow’s the time to explore the artsy side of Chicago with a visit to one of the country’s most prestigious art museums, also voted one of the best museums in the world on Trip Advisor!

The Art Institute of Chicago features celebrated collections of modern and contemporary art, architecture, design, and photography, as well as Impressionist painting, decorative arts, and more.

Some of the most famous pieces at the Art Institute include the Chagall stained glass windows, Grant Wood’s American Gothic, Matisse’s Bathers by a River, and Georgia O’Keeffe’s Black Cross, New Mexico.

We recommend reserving at least 2 hours for this attraction, perhaps more if you’re an art lover.

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

Stop #3: Millennium Park (free!)

Chicago Bean 1Take some time to stroll around this beautiful urban greenspace. Be sure to note highlights like the Pritzker Pavilion – an architectural marvel – and the charming Lurie Garden.

You can also explore some of the park’s iconic works of art. Be sure to check out the Crown Fountain and the Cloud Gate sculpture (also known as the Bean, pictured above). Get you cameras at the ready when you’re at the Bean. It’s one of Chicago’s most recognisable spots and a go-to for a vacation snap!

There will also be a number of special events going on in the park from late spring to early fall. Do a little research before your visit to see what’s on. You can expect everything from prestigious concerts to fund food festivals to free yoga.

We recommend reserving about 1 hour to explore the park; more if you’re participating in an event.

Getting In: It’s free to explore Millennium Park, but any additional activities may incur extra costs not covered by the pass.

Save on this 3 Days in Chicago itinerary

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Let’s Recap

So doesn’t that sound like a fantastic 3 days in Chicago?

With a great mix of art, culture, entertainment, education, and just plain fun, we know this Chicago itinerary will please first-time visitors and returning customers alike. Don’t forget to make the most of your evenings in Chicago too. Check out our Chicago nightlife guide for some more fun ideas to add to your itinerary.

Visit each of these attractions with a 3-Day Go Chicago® Card and save big on combined admission costs.

You’ll also be able to save even more with included extra discounts on dining, shopping, and additional attractions.

Go Chicago Card

The information contained in this post, to the best of the author's knowledge, was accurate at time of publishing. We do our best to ensure and maintain the accuracy of this information.


  1. Frank Antoniello says

    We are looking at the Go Chicago card for 3 days but there is no price anywhere for myself and the wife. Please advise.

    • Smart Destinations says

      You can see all of our current prices, passes, and included attractions on the Go Chicago Card here – pass=Chi_Prod_Go

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