Chicago 2021 Holidays

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Accommodation, flights, car rentals, things to do and more - for your holiday in Chicago choose Expedia! Find everything you need to organise your trip to Chicago in one place. Enter your dates in the search bar above or scroll to our top deals below!

Where to stay in Chicago

Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago

Top hotels in Chicago

The Whitehall Hotel
The Whitehall Hotel
4 out of 5
105 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €85 per night from 22 Nov to 22 Nov
3.9/5 Very Good! (3,311 reviews)
"Great location - less touristy than the loop but still easily walkable to all the popular destinations, but with better food options and great shopping nearby. Hotel is basic and old but the rooms are large for a downtown hotel. Our beds sucked and desperately need to be replaced, giant dips in the ..."

Reviewed on 19 Oct 2021

The Whitehall Hotel
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
4 out of 5
300 E Ohio St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €126 per night from 22 Nov to 22 Nov
4.2/5 Excellent! (1,587 reviews)
"Walking distance to shopping & restuarants"

Reviewed on 18 Oct 2021

DoubleTree by Hilton Chicago - Magnificent Mile
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €100 per night from 21 Nov to 21 Nov
3.7/5 Good! (4,075 reviews)
"Great location. Amazing courteous helpful staff."

Reviewed on 20 Oct 2021

Congress Plaza Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top things to do in Chicago

Chicago Holiday Packages

A modern metropolis on the shores of Lake Michigan that’s defined by a love for fine art, baseball and the blues.

Stroll museums and parks filled with art, and catch live blues any night of the week in Chicago’s bustling Downtown district. Or catch a lively sports game in this home to the Cubs and White Sox baseball teams, and the Chicago Bulls basketball team.

This metropolis is the third largest city in America, but getting around is easy thanks to the efficient above ground train, the ‘L’. Get your bearings from the tallest skyscraper in the US, Willis Tower, which defines the city’s skyline. The viewing platform, 1,353 feet (412 metres) above the busy streets, offers unparalleled vistas of Lake Michigan, Navy Pier, and other main attractions. 

Lincoln Park, just north of downtown, has beaches, sporting grounds and landscaped gardens. Soak up the history of the Windy City at the Chicago History Museum, located on the southern end of the park. Take a stroll through the indoor gardens of the Lincoln Park Conservatory, or spend an afternoon at the Lincoln Park Zoo. This public zoo houses more than 1,000 animals. Brookfield Zoo, 12 miles west of the city centre, is more than double the size and features dolphin displays, big cats, a variety of primates and more. 

Head back into the Loop district downtown for some of the best shopping in the city, along Michigan Avenue’s Magnificent Mile. It’s a good place for lunch or dinner, or people watching while you sip a coffee or beer. Just south of the Magnificent Mile is the expansive Art Institute of Chicago well worth a visit for its collection of European and American masterpieces that include Monet, Van Gogh, and much more. Nearby is Millennium Park, a meeting place with public art and spectacular summer concerts.  

Chicago’s Museum Campus is located in the South Loop, just a few miles by car or a few stops on the “L” from downtown. The Field Museum is filled with natural history, while the Museum of Science has interactive exhibits such as a mock coal mine and an airplane.

Some of America’s most influential figures came from Chicago. Visit the Ernest Hemingway Museum and House, where the famous writer was born. Architect Frank Lloyd Wright’s first house is in the pretty Oak Park neighbourhood (called the Frank Lloyd Wright Home and Studio). He designed many houses and buildings in the area, including Unity Temple, considered one of his best. On your way back into town, stop off at the Garfield Park Conservatory, an urban oasis of rare and exotic plants.

No trip to Chicago would be complete without catching a baseball game at the legendary Wrigley Field. At night, head to Navy Pier, packed with lively bars and restaurants. Another option is to head out for a night of blues at one of Chicago's legendary clubs. Check out  B.L.U.E.S. near downtown on Chicago's north side or Kingston Mines a few miles north near Lincoln Park. Both of these long established venues have music every night of the week.

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