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.

Getting to Chicago

By Plane

O'Hare International Airport Chicago's O'Hare is one of the world's busiest airports. It's about 15 miles northwest of the Loop in downtown Chicago. O'Hare has 5 terminals, all of which have information booths and multilingual employees to assist you.

If you have a lot of baggage and want to get into town by car, you have 2 main options: taxis or GO Airport Express. Taxis are everywhere at the airport, and it will cost you about $35 to get downtown. Airport Express vans must be reserved ahead of time ( and provide service to most hotels in Chicago. For either option, you can expect the ride to downtown to take at least 30 minutes, but up to 2 hours in heavy traffic (you'll definitely want to avoid rush hour).

Public transportation is another option if you want to save money, and there's no need to worry about traffic. From O'Hare, the Blue Line takes you downtown in about 40 minutes for only a few dollars. Trains leave every 6-10 minutes during the day and every half-hour in the evening and overnight.

Midway International Airport Although it's smaller than O'Hare, Midway is closer to the Loop and services more discount airlines (but fewer airlines overall). If you're looking for a good deal on plane tickets, check out flights to Midway first.

The options for getting into town by car are similar to those for O'Hare—taxis and Airport Express vans are both easily available (reservations required for the latter). The car ride takes about 20 minutes without traffic and will run you about $25. Again, you'll want to avoid rush hour traffic.

Getting downtown from Midway by public transportation is fast and easy, but the Orange Line, which services Midway, stops operating between the hours of 11:30 PM and 5:00 AM (so plan accordingly). For those traveling with lots of luggage, beware that the train station is a good walk from the terminal. Apart from those disadvantages, the Orange Line is quite convenient—it runs every 6-15 minutes, costs only a few dollars, and takes about 25 minutes to get downtown.

Getting Around Chicago

Public Transportation

The Chicago Transit Authority (CTA) runs the 2nd largest public transportation system in the nation, servicing the City of Chicago and 40 neighboring communities. The CTA provides over 140 bus routes, including some 24-hour routes, known as "Owl Service." The CTA also has a rail system that consists of 8 "rapid transit trains" (like the subway or metro in other areas).

In Chicago, these rail lines are referred to as the 'L,' which is short for "elevated," although today some parts of the system are below ground. The Red Line and the Blue Line operate 24 hours, every day.

For more information, visit the CTA website.


It's easy to hail a cab in the central areas of Chicago but with gas prices high and passenger fees climbing, it can get pretty expensive. However, if you're willing to pay the price, taxis are a great way to get around the Loop and to dining, shopping, and entertainment options beyond downtown, like Near North Side, Old Town, and Lincoln Park.

On Foot

Walking is perhaps the greatest way to experience Chicago. Several of Chicago's top attractions are located within walking distance of the area's popular downtown hotels. Of course, walking is not always convenient - particularly when traveling far distances or in inclement weather. However, when you get the chance, walking is a feasible and inexpensive option.

Chicago Neighborhoods

When it comes to neighborhoods in Chicago, there aren't really official geographical boundaries. Even the most official map, showing 200+ neighborhoods, was created in the 1970s by researchers that went door-to-door asking the question, "What neighborhood is this?"

Regardless, Chicago's neighborhoods are notoriously dynamic and commonly referenced. Here is a brief guide to some of the most popular areas in inner Chicago.

The Loop

When you hear people refer to "the Loop," they're talking about the city's downtown area, bordered by the Chicago River to the north and west, by Michigan Avenue to the east, and Roosevelt Avenue to the South. Quite literally, this focal area of high-rises is surrounded by a loop of elevated train tracks.

Magnificent Mile

Many of the city's best hotels and most concentrated shopping and dining are found on this stretch of Michigan Avenue. The Magnificent Mile runs from the bridge spanning the Chicago River to its northern pint at Oak Street (although Michigan Ave extends far longer).

River North

This area west of the Magnificent Mile is an old warehouse district. However, it is now home to many of the city's most popular restaurants, night clubs, and art galleries, making it a significant commercial district.

Museum Campus

This 57-acre park comprises the southeast corner of the celebrated urban Grant Park, along the Michigan Lake waterfront. It houses 3 of the city's most famous museums, Shedd Aquarium, Adler Planetarium, and The Field Museum.

Navy Pier

The Navy Pier is the Midwest's #1 tourist and leisure destination, attracting locals and vacationers alike. On this 3,300-foot pier on Lake Michigan, you'll find rides, entertainment, restaurants, shopping, cruises, and more.

Lincoln Park

It's the name of Chicago's most popular residential neighborhood for young singles and families, and also the name of the huge park that borders this neighborhood to the east. The park is home to one of the nation's oldest zoos.

Chicago Accommodations

Hilton Chicago

The Hilton Chicago is located in the South Loop, right by Museum Campus, making it perfect for families who are headed to the major museums. It's also close to Grant Park, where kids can run around. The hotel itself features magnificent public areas like the Grand Stair Lobby and the Grand Ballroom, but the rest of the hotel is pretty typical of any modern hotel chain. It's a big and busy place, ideal for family vacations, but not for romantic getaways.

Central Loop Hotel

Located in the center of the Loop (of course) this hotel is walking distance from The Willis Tower (former Sears Tower) and the Magnificent Mile. In the hotel you'll find comfortable and stylish furnishings, an on-site Elephant & Castle, and a 24-hour concierge. It's a good value for the clean rooms, helpful staff, and prime location.

The Tremont Chicago Hotel at Magnificent Mile

It's not a luxury resort, but this hotel offers you a cozy place to stay for a good price. It has a "homey" atmosphere, rather than the "modern" feel most chains go for. Don't expect high-end amenities, but you'll find a restaurant, a small exercise room, and other basic services. Plus, you're only one block west of Michigan Ave, putting you in great position to shop the Magnificent Mile.

Hyatt Regency Hotel

The Chicago Hyatt is a notable building, rising 33 stories about the convention center. It's got all the amenities of a luxury hotel and a great location minutes from Museum Campus and the Loop. The hotel also offers a complimentary shuttle to downtown shopping areas, the main museums, and Navy Pier. In the rooms, expect contemporary furnishings, small bathrooms, and scenic views.

Chicago's Essex Inn

The best part of the Essex is that it's centrally located in the business district and offers easy access to pretty much anywhere you'd want to go in Chicago. It's a 3-star hotel with an indoor pool, on-site restaurant, fitness facility, bar/lounge, and conference/business rooms. The rooms are average size, but bright and airy.

Red Roof Inn Chicago

This one's for all the budget-conscious travelers who still want to stay in downtown Chicago. The location right off the Mag Mile is the main selling point. Rooms are small and minimalist, but clean and somewhat new. The bathrooms are also tiny but very clean. You won't find many amenities, but it's a great deal if you're not planning to spend much time in the hotel.

Chicago Itinerary

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.

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