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Most Frequently Booked Chicago Hotels

Top Cheap Chicago Hotel Deals

Top Luxury Chicago Hotel Deals

Other Travelers Recently Booked These Chicago Hotels

How Much is a Hotel Room in Chicago?

Hotels in Chicago start at $40 per night. Prices and availability subject to change. Additional terms may apply.


Inspired Chicago Travel Tips

How to Have the Perfect Chicago Weekend

Chicago offers a full agenda for any weekend visit. To narrow down the options for a perfect trip, we’ve partnered with family traveler (and Chicago resident) Kirsten Maxwell from Kids Are A Trip. She shares some favorite things to do and places to eat to have the perfect Chicago weekend. Chicago is a city that […]

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Best Events to Celebrate the Holidays in Chicago

The arrival of December brings a flurry of holiday magic to the Windy City, with locals and tourists bundling up and heading out to enjoy the season despite the cooler temperatures. Chicago local Kirsten Maxwell of Kids Are A Trip shares some of the holiday season’s highlights you won’t want to miss. The holidays in Chicago are a wonderful […]

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Summertime in Chicago: The Best Things to Do

When warm weather arrives in Chicago, tourists and locals alike head out to enjoy the endless number of Windy City activities and copious amounts of sunshine. We’ve partnered with Kirsten Maxwell of Kids Are A Trip to give us the inside scoop on the best things to do in Chicago in the summertime.  1. Take a tour of the […]

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What are the top landmarks in Chicago?

Don’t miss these must-see sights and attractions

Kirsten Maxwell  Getting to Chicago

Kirsten Maxwell Gnational Gnomad

Chicago has two major international airports: O’Hare (ORD), which is 17 miles northwest of downtown and Midway (MDW), just 10 miles southwest of the city. Transportation from both of these locations is plentiful and comes in the form of city trains, taxis, and rental cars. Expect it to take anywhere from a half hour to an hour to reach downtown, depending on the time of day. It is also possible to arrive via Amtrak. The main train depot—Union Station—is in the heart of the city.

Where To Stay In Chicago

Centrally Located Hotels:

Chicago Marriott Magnificent Mile
InterContinental Chicago

Best Luxury Hotels:

Best Family-Friendly Hotels:

Getting Around Chicago

Most major attractions are located in the heart of downtown. The city is perfectly manageable using public transportation, taxis, Uber/Lyft, and your own two feet. Chicago Transit Authority (CTA) operates the buses and trains, and METRA runs trains to the outlying suburbs. If you want to explore the area on your own time, consider renting a car.

TIP: Chicago traffic can be stressful—especially during rush hour, on the weekend, and during major sporting events or festivals. Summer is construction season, and you’ll see plenty of snow during the winter. If this concerns you, stick with public transportation.

What Not to Miss In Chicago

Willis Tower or 360 Chicago

For a true overview of the city, head up. Both the Willis Tower and 360 Chicago offer fantastic views of the city from towering heights. The Willis Tower  has “The Ledge,” a glass box that extends out from the building, allowing unobstructed views of the city 1,353 feet below. Still haven’t quenched your thirst for heights? Head to 360 Chicago, located in the John Hancock Center, and check out “Tilt.” Visitors enter a glass cage that tilts away from the building and gaze out over the city from a height of over a thousand feet. Neither experience is for the faint of heart!

Art Institute of Chicago

The Art Institute of Chicago was named the top museum in the world by Trip Advisor in 2014, and it houses one of the largest permanent collections in the United States. Some of the featured artists include Picasso, Monet, and Rivera, but there are thousands more to admire.

Millennium Park

Millennium Park is centrally located parallel to Michigan Avenue and Lake Michigan, and it’s the perfect place to gather with a group of friends. During the summer there are free concerts, performances, and festivals, and during the rest of the year it is a great place to relax and people-watch. The main attraction is the “Cloud Gate” sculpture. Most Chicagoans refer to it as “The Bean” because it looks like, well, a giant silver bean. Chicago’s skyline reflects from all its shining sides, and you can even walk underneath the sculpture.

Adjacent to this is the Crown Fountain. The fountains are actually two 50-foot towers that display images of Chicago residents on a giant video screen. When the face on the screen smiles, water comes pouring from their mouth, dousing the eager children gathered below.

Between Millennium Park and the waterfront is the beautiful Maggie Daley Park. With playgrounds for all ages, an ice skating ribbon in the winter, and a rock climbing wall, it is a magical escape in the city for families.

The Beach

It’s hard to miss the 26 miles of Lake Michigan shoreline that borders downtown Chicago. The beaches are open to the public, so find a beach near your hotel, grab your towels, and walk or take a taxi to the shoreline of your choice. Montrose Beach, North Avenue Beach, and Oak Street Beach are all worth a visit.

Where to Eat

Chicago is a city made for foodies—there’s almost too many good restaurants to list. Obvious choices for deep dish pizza are Giordano’s, Pequod’s, and Lou Malnati’s. Craving a Chicago dog? Head to Portillo’s and be sure to grab a slice of chocolate cake for dessert. Want to try one of the better restaurants in town? Find something owned by Rick Bayless (Xoco, Frontera Grill), the Boka Group (Girl & The Goat, Boka), or Paul Kahan (The Publican, Big Star) —you won’t be disappointed. Don’t forget to try multiple servings of the cheese and caramel popcorn (Chicago mix) at Garrett Popcorn, because there is nothing like the original.

Recent Chicago Hotel Reviews By Fellow Wanderers

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