The Best of Chicago in 3 Days Itinerary

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, traditional food, 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 Best of Chicago 3-Day Itinerary.

We've done all the research and planning to get you to as many top attractions as possible. And we didn't just stop with attractions, we've also scoped out the best restaurants and activities, too.

By following this itinerary, you'll optimize your savings with Smart Destinations.

Day 1: The Loop/Downtown Chicago

Attractions: The Art Institute of Chicago, Millennium Park, and SkyDeck Chicago (former Sears Tower)

Dining: Yolk, The Gage, and Giordano's

9:00 AM: Breakfast at Yolk

Start your first day in Chicago with a hearty breakfast at Yolk, right in the Loop on S. Michigan Ave. It's perfect location for your first stop in Chi, and has been voted #1 Breakfast in Chicago for its innovative meals, specialty juices, and own private labeled premium coffee.

10:15 Catch the Bus to The Art Institute

After breakfast head to The Art Institute of Chicago. Walk up S. Michigan St. to the bus stop at Jackson St. Take the 4 Bus (toward Illinois Center) about 5 minutes up Michigan to Monroe. Get off and you'll be right in front of the Institute.

10:30 AM: Visit The Art Institute of Chicago

Get to the museum right when it opens. Not only is The Art Institute of Chicago a world-renowned art museum, it's also the second largest museum in the nation. Plan to spend about 2-3 hours in the museum. You won't be able to see everything, but you'll be able to see a good amount. If you're an art-lover, plan ahead to navigate to your favorite works.

1:30 PM: Lunch at The Gage

Next, stroll across the street to The Gage Restaurant and Tavern, steps away from Millennium Park. They offer upscale comfort food but it's still possible to get a great meal at a reasonable price. Although The Gage has ample seating, you may want to make a reservation as restaurants right on the Park get quite busy.

3:00 PM: Explore Millennium Park

You're already at Millennium Park, a Chicago landmark, so why not explore? This park and gathering spot features art and architecture that is unparalleled in design. Plus, you'll find fun free events, like musical performances, exhibitions, and tours. Of course, you can always just spread out on the lawn and enjoy some downtime, weather permitting.

4:00 PM: Pink Line to SkyDeck Chicago

From the Millennium Park entrance, continue on East Madison St. until you get to Wabash St, about a block away. From here, catch the Pink Line towards 54/Cermak and get off at the Quincy/Wells stop (about 6 min). Now you're just a short 5 minute walk from your next stop.

4:30 PM: Ride to the Top of Willis Tower - SkyDeck Chicago

This is the highlight of any Chicago trip and voted one of the "7 Wonders of Chicago." The SkyDeck is the name of the observation deck at the top of the former Sears Tower, now renamed the Willis Tower. Check out 360-degree views, engage in interactive exhibits, and - if you dare - climb on out to The Ledge, 4 enclosed glass balconies extending 4 feet outside the building.

6:30 PM: Dinner at Giordano's

For dinner, get your fill of Chicago's famous deep-dish "stuffed" pizza at Giordano's, voted "Best Pizza in America" by NBC. Giordano's is a short walking distance from Willis Tower - simply walk south on S. Wacker Drive and turn left onto W. Jackson Blvd.

Suggested Evening Activities in the Loop

Buddy Guy's LegendsJazz Club
Stop in Buddy Guy's to experience Chicago's finest blues music and to enjoy some southern Cajun soul food. You can either buy tickets in advance or just pay the cover at the door. This place is a classic Chicago gem for any music-lover.

South Loop ClubNeighborhood Sports Bar
You'll find walls lined with sports memorabilia and large-screen TVs reporting the latest stats at this S. State St. bar. They have 12 on-tap beers and an assortment of classic bar food.

Ford Center for the Performing Arts Oriental TheatreBroadway in Chicago
You'll need tickets ahead of time, but if you can catch a production at The Oriental Theatre, you're in for a treat. The Theatre has housed many productions direct from Broadway and the world premieres of productions destined for Broadway. You'll also enjoy the theatre's rich history as a deluxe movie palace opened in 1926.

Chocolate Buffet at the Peninsula Hotel ChicagoDessert
Come to one of the grandest hotels in Chicago and delight in an all-you-can-eat chocolate buffet from 8-11 PM every Friday and Saturday. It's a little pricey, but the variety and quality of chocolate is incomparable.

Day 2: Navy Pier and the Mag Mile

Attractions: Magnificent Mile, Architectural River Cruise, and Navy Pier

Dining: Oak Tree Restaurant & Bakery, House of Blue Back Porch Restaurant, and Billy Goat Tavern

8:30AM: Breakfast at Oak Tree Restaurant & Bakery

Begin day 2 with breakfast at a classic and newly renovated neighborhood favorite, the Oak Tree Restaurant & Bakery. It's in the heart of the Gold Coast and at the beginning of the Magnificent Mile, right in the 900 Shops Mall. Their breakfast fare is so good they serve it all day long.

9:30 AM: Start Your Trek down the Magnificent Mile

Since you're already there, start your Mag Mile adventure at the 900 North Michigan Shops. Make sure to stop in the world-famous Bloomingdale's and check out high end-stores like Michael Kors and Gucci. If you're a die-hard shopper, visit all 6 floors.

Continue traveling south down the Magnificent Mile (N. Michigan Avenue). Some places to stop are the shops at Water Tower Place (Godiva Chocolatier, The LEGO Store, and American Girl Place are a few specialty classics), the two-story Tiffany & Co., HERSHEY'S Chicago, and the Shops at North Bridge.

12:30 PM: Lunch at the House of Blues Back Porch Restaurant

When you're done with shopping on N. Michigan, cross over to Dearborn St and head south to the House of Blues, where you'll eat dinner at the Back Porch Restaurant. Make sure to present your Go Chicago Card to take advantage of your "buy one lunch entrée, get one free" special.

2:00 PM: 29 Bus to the Navy Pier Terminal

After lunch, walk about 3 minutes to the bus stop at State St. and Kinzie. From here, get on the 29 bus to the Navy Pier Terminal. The ride will take about 10 minutes.

2:30 PM: Redeem Tickets fo rthe Architectural River Cruise

Present your Go Chicago Card at the Navy Pier Ogden Slip ticket booth, and redeem your tickets by presenting your Go Chicago Card.

3:00 PM: Architectural River Cruise

Depart on your 1-hour narrated cruise, featuring all of Chicago's greatest architectural landmarks. The cruise departs from Ogden Slip at Navy Pier. The cruise will also bring you back to Navy Pier.

4:00 PM: Head to Navy Pier Park Attraction Ticket Booth

After your tour, it's time to explore the world-famous Navy Pier. First, you'll want to pick up your 5-ride Combo Ticket at the any of the park's attraction ticket booths. Make sure you do this before 5:30.

In the Evening: Why Not Explore Navy Pier?

Spend your evening exploring all the entertainment that the Navy Pier has to offer. Your 5-Ride Combo Ticket will get you on the famous Navy Pier Ferris Wheel, as well as the Carousel, the Light House, The Links Mini-Golf Course, and the Wave Swinger thrill ride.

Some other Navy Pier options include shows at the IMAX Theater, Cirque Shanghai, and the Family Pavilion Stage. Plus, discover unique dining and shopping choices. In the summer, you can catch a fireworks show on Wednesdays and Saturdays at dusk.

Dinner on Chicago's Navy Pier: Billy Goat Tavern

When you get hungry, navigate your way to the celebrated Billy Goat Tavern, of Saturday Night Live and "Cubs Curse" fame. The American restaurant, best known for its burgers, has been gathering fame since its opening in 1934 and is a Chicago must-see.

Day 3: Museum Campus

Attractions: The Field Museum, Adler Planetarium, Shedd Aquarium, Grant Park, and Buckingham Fountain

Dining: Bongo Room, Café Galileo's, and Lou Malnati's

8:00 AM: Breakfast at Bongo Room

Treat yourself to breakfast at the Bongo Room, where many breakfast entrees could double as dessert. If you're not into white chocolate and cheesecake pancakes, savory omelets and breakfast burritos will satisfy your taste buds.

9:00 AM: Ride or Walk to Museum Campus

From Bongo Room, either catch the 130 bus to the Soldier Field & Field Museum stop, or walk about 15 minutes to Museum Campus.

9:30 AM: Start Your Museum Tour at The Field Museum

Discover the best of the natural sciences from the world's largest T-Rex fossils to the largest collection of gems in the world at one of the nation's top museums.

11:30 AM: Walk to the Adler Planetarium

From the Field Museum, it's a quick 10-15 minute walk down E. Solidarity Drive to the Adler Planetarium.

12:00 PM: Adler Planetarium & Astronomy Museum

Explore outer space without leaving Chicago at the renowned Adler Planetarium. All exhibits and most shows are included free with your Go Chicago Card.

2:00 PM: Lunch at Café Galileo's

Enjoy an award-winning view of Chicago while you dine in the Adler's on-site café. Choose from a unique menu of paninis, toasted subs, classic sandwiches and salads, or individual pizzas.

3:00 PM: Circle back to Shedd Aquarium

Continue on E. Solidarity Drive for a 10-minute walk to the Shedd Aquarium.

3:30 PM: Visit the World-Famous Shedd Aquarium

Your last stop on Museum Campus will be to Chicago's biggest museum attraction, Shedd Aquarium, where you'll enjoy skip-the-line privileges. You'll want to spend a couple hours exploring this incredible underwater world.

6:00 PM: In Transit to Dinner

Either walk 15 minutes, going west on E. Roosevelt and taking a right on S. State Street, or walk down E. Roosevelt to the bus stop at Roosevelt and Michigan and ride from there to State & 9th Street.

6:00 PM: Dinner at Lou Malnati's

You can't leave Chicago without dining at Lou Malnati's, the oldest name in Chicago pizza. You'll enjoy the best of deep-dish and thin crust at this historic Chicago pizza joint. Present your Go Chicago Card to receive $5 off a large pan pizza.

Evening: Grant Park & Buckingham Fountain

Spend your evening strolling through Chicago's "front yard," Grant Park. At dusk, you'll get to see the Buckingham Fountain in all its glory, when the 20-minute water show is complete with choreographed lights and music.

Buy Now & Save!

With this 3-day itinerary, you'll pay less than the gate prices for the top Chicago attractions. Plus, you'll get great discounts on meals and activities with your Go Chicago Card. Your Go Chicago Card will include admission into all of our Chicago attractions, so feel free to alter our itinerary to meet your needs.

Save 20% to 55% on Chicago's Top Attractions

Build Your Own Custom Pass

Save
20%
  • Bundle 2+ attractions
  • Save a guaranteed 20%

All-Inclusive Pass

Save
up to
55%
  • 20+ attractions
  • One low price
  • Save up to 55%

Chicago Travel Tips