Chicago Itinerary – 3 Days in Chicago for First Timers

Chicago is a city that tourists simply can’t get enough of. But that comes as no surprise because Chi-town offers diverse cultural experiences, world-class museums, exciting culinary adventures, renowned architecture, and some of the nation’s favorite attractions.

Most Chicago visitors don’t have enough time to do everything in one trip, and it can be difficult to decide what to do and when to do it.

However, that just got a whole 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.

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

This 3 day itinerary includes:

  • Big Bus Chicago Hop-On Hop-Off Bus Tour
  • Shedd Aquarium
  • The Field Museum
  • Adler Planetarium
  • Chicago Theatre Tour
  • 360 CHICAGO
  • Chicago Children’s Museum
  • Navy Pier Centennial Wheel & Rides
  • SkyDeck Chicago
  • The Art Institute of Chicago
  • Millennium Park (free!)
  • Chicago Architecture Foundation

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

chicago-bus-tourThis attraction is your perfect introduction to the Windy City. Your Chicago Hop-On Hop-Off Bus Tour will take you past all the top attractions and landmarks, and tour 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, 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 this for transportation).

Remember to pick up your ticket in advance of boarding. Your ticket is also good for two full days, so feel free to use it tomorrow!

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

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.”

Proceed to Will Call for admission. We recommend reserving at least 2-3 hours for this attraction.

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

Lunch near the Museum Campus

The area immediately to the west of the Museum Campus is filled with plenty of dining options, from casual sandwich shops to pizza and pitas (there’s even a Trader Joes if you’d prefer something organic).

If you’re looking for something a bit more adult-friendly, check out The Scout Waterhouse + Kitchen, with a great beer list and upscale sports bar vibe.

Stop #3: The Field Museum

The-Field-Museum-2After 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 is 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 theatres, and the historic Atwood Sphere experience, you’ll practically never run out of things to see and do.

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.

Dinner in the South Loop

This neighborhood is a great place to explore to discover your new favorite restaurant. You’ll find everything from popular, family-friendly chains to indie restaurants and trendy gastropubs.

If you’re looking to dine Chicago-style, stop by Lou Malnati’s for some deep-dish pizza.


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 and actresses. 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, see the walls with tons of celebrity autographs scrawled across them, and check out the historic photo exhibits.

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)

Shoreline-Architectural-River-Cruise-2Start off your morning with a beautiful cruise down the Chicago River.

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 (at the Hancock Tower)

360-Chicago-John-Hancock-Tower-2360 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.

Lunch on the Magnificent Mile

Once you leave 360 CHICAGO, wander along Michigan Avenue (a.k.a. the Magnificent Mile) in search of your next meal.

You’ll find plenty of options, especially if you explore side streets. The nearby Water Tower Place Mall has several delicious restaurants, too, which can be more affordable than some of the other options you might wander into on Michigan.

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-1When you return your bike rental to Navy Pier, 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® Card 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.

Dinner on Navy Pier

Why venture elsewhere when there are so many dining destinations right nearby?

You’ll find the iconic and delicious Harry Caray’s Tavern and Bubba Gump Shrimp Co., plus a more general food court and a Margaritaville the adults may enjoy. Consider trying a Chicago-style hotdog!


Stop #1: SkyDeck Chicago

skydeck-chicagoCheck 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

art-institute-of-chicago-museumsNow’s the time to explore the artsy side of Chicago with a visit to one of the country’s most prestigious art museums, also recently voted the #1 Museum 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.

Lunch in Millennium Park

You could choose to eat at the Art Institute itself, at the famed Terzo Piano restaurant, or at one of the many restaurants that surround this urban cultural park.

The Park Grill is a favorite with visitors and serves a wide variety of cuisines and drinks.

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, like the Crown Fountain and the Cloud Gate sculpture (also known as the Bean, pictured above).

Getting In: We recommend reserving about 1 hour to explore the park.

Stop #4: Chicago Architecture Foundation

Pritzker Pavilion ChicagoTo complete your education in Chicago’s architectural history and culture, stop by the Chicago Architecture Foundation and pick up one of their many walking tours. Each tour has a different theme and covers different parts of the city (as well as various lengths).

You’ll also find a variety of free, informative exhibits about architectural history, contemporary developments in building standards and aesthetics, and the modern sustainability movement.

You even have the option to enjoy lectures by local experts (check the schedule before your arrival to see if you can catch one!).

Tour length varies, but we recommend reserving at least 1 hour for your tour.

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

Dinner in the Loop

The area surrounded by Wacker Drive, the Loop is a neighborhood filled with tons of great restaurant options ranging across all price points and cuisines. Sweetwater Tavern and Grille is a visitor’s favorite, with a nice diverse selection of food and a great drink list.

Or, if you haven’t had a chance yet, try a Chicago-style hotdog or deep-dish pizza.

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.

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


  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.

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