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Holidays in Chicago

Choose two or more items and save on your trip:

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

Estimated price for 1 night / 2 adults
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by Hilton
4.5 out of 5
85 East Wacker Drive, Chicago, IL
Free cancellationReserve now, pay when you stay
The price is AU$207 per night from 19 Oct. to 20 Oct.
4.6/5Wonderful! (2,409 reviews)

"We were met by a friendly staff member who went out of his way to help us feel welcome and informed about how the elevator system worked. He even escorted us up to the check in desk upstairs. Awesome experience from start to finish!"…"

Reviewed on 17 Sep. 2020

LondonHouse Chicago, Curio Collection by Hilton
Sofitel Chicago Magnificent Mile
Sofitel Chicago Magnificent Mile
4.5 out of 5
20 E Chestnut St, Chicago, IL
Free cancellationReserve now, pay when you stay
The price is AU$230 per night from 18 Oct. to 19 Oct.
4.6/5Wonderful! (1,774 reviews)

"Amazing experience! Nice location and amazing beds!!!!!"…"

Reviewed on 9 Sep. 2020

Sofitel Chicago Magnificent Mile
Best Western Grant Park Hotel
Best Western Grant Park Hotel
2.5 out of 5
1100 S Michigan Ave, Chicago, IL
Free cancellationReserve now, pay when you stay
The price is AU$99 per night from 27 Sep. to 28 Sep.
4.1/5Very Good! (3,011 reviews)

"Location is the best feature. Lots of restaurants, museums, train stations nearby"…"

Reviewed on 13 Sep. 2020

Best Western Grant Park Hotel

Top activities in Chicago

360 CHICAGO Observation Deck (Hancock Center)
Image for 360 CHICAGO Observation Deck (Hancock Center)

360 CHICAGO Observation Deck (Hancock Center)

AU$35
Per adult
86% of travellers recommend
Go Chicago Explorer Pass: Choose 3, 4 or 5 Top Attractions
Image for Go Chicago Explorer Pass: Choose 3, 4 or 5 Top Attractions

Go Chicago Explorer Pass: Choose 3, 4 or 5 Top Attractions

AU$117
Per adult
80% of travellers recommend
The Field Museum
Image for The Field Museum

The Field Museum

AU$36
Per adult
92% of travellers recommend

Save Time and Money with Chicago Holiday Packages

Get instant savings by booking a Chicago holiday package. Just pick your favourite options and let Expedia take care of the rest. If you book a package deal on Expedia, you can save as much as $583*. Look around our universal database of more than 550 airline partners and 1,000,000 properties worldwide. Too many to select from? Don't worry — we'll help you decide! If you change your plans, we will honour your cancellation request on almost all bookings with no extra fee.

Places to Visit in Chicago

Preparing for your trip to Chicago? Need some info about what to see when you arrive? That's where we can assist! Take it from us, your bucket list will be heaps shorter after a trip to Chicago! Famed attractions like the Art Institute of Chicago and Willis Tower should be some of your first ports of call. The McCormick Place and the University of Illinois Chicago also draw in crowds of travellers from all across the globe. You're going to find yourself surrounded by terrific things to do and see, including Navy Pier and the Lincoln Park Zoo. If you're dying to get the most out of your stay, also check out Lincoln Park and the Chicago Cultural Centre. Millennium Park is an oasis amid the bustle of everyday life. Pull off your shoes and feel the cool grass beneath your feet or simply lie on your back and spot shapes in the clouds. Adventurers in this destination have heaps of options. Those who are a little queasy around heights might want to look away, but anyone who's curious about skyscrapers can't miss John Hancock Centre. Towering high above the ground, it's a beloved fixture of the area's skyline. Still have some time on your hands? Want to catch a sunrise among some spectacular scenery? Skydeck Ledge boasts glorious views that deserve to be photographed.

When we hark back to our travels, we usually remember experiences rather than our swish hotel room and its view of the pool. Are you ready to create some new travel memories? Your trip to Chicago is about to get a lot more exciting. There are heaps of activities available, such as:

To check out all the activities on offer, head to our Chicago things to do page.

Chicago Accommodation

With no less than 165 accommodation in Chicago, finding a place to stay won't be difficult. But why wait around? Book now via Expedia and kick-start your next cheap holiday or luxury getaway. Begin the quest for a dreamy Chicago base by looking into the latest offers at the Chicago Premier Suites (540 N State Street) and The Peninsula Chicago (108 East Superior Street). Alternatively, the Trump International Hotel & Tower Chicago (401 N Wabash Ave) and the Old Chicago Inn (3222 N Sheffield Ave) are two properties well worth investigating if you're travelling on the cheap. If you'd rather stay nearby the Art Institute of Chicago, The Langham, Chicago and the JW Marriott Chicago are excellent options.

Nearest Airports to Chicago

We know the airport won't be the most memorable moment of your holiday, but there's nothing like the excitement of knowing that your well-deserved trip to Chicago is just a flight away! Once you unbuckle your seatbelt at Midway International Airport (MDW), you'll be 9 miles from the heart of town.