Chicago Holidays
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Our guide on where to stay in Chicago
Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Chicago Holiday
Our pick of the best Chicago Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$268 per night from 14 Feb to 15 Feb
NZ$268
14 Feb - 15 Feb
includes taxes & fees
8/10 Very Good! (9,790 reviews)
Really interesting place, great price for the location too. Staff was very friendly.
Reviewed on 19 Jan 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$307 per night from 1 Feb to 2 Feb
NZ$307
1 Feb - 2 Feb
includes taxes & fees
8.4/10 Very Good! (2,576 reviews)
Did not have breakfast
Reviewed on 19 Jan 2026
The Royal Sonesta Chicago Downtown
71 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$318 per night from 30 Jan to 31 Jan
NZ$318
30 Jan - 31 Jan
includes taxes & fees
9.2/10 Wonderful! (3,260 reviews)
GREAT HOTEL
Reviewed on 22 Jan 2026
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.
Discover the most popular places to visit in Chicago
Wrigley Field
A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.
McCormick Place
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
Navy Pier
One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.
What to do in Chicago
Chicago: Navy Pier Centennial Wheel Ticket
NZ$43
per adult
88% of travellers recommend
Chicago Crime and Mob Bus Tour
NZ$85
per adult
92% of travellers recommend
Explore a world of travel with Expedia
- Cottages in Rush Street
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- Chicago Hotels
- Hotels near Michigan Avenue Bridge
- Streeterville Hotels
- Hotels near Grant Park
- Hotels near Field Museum of Natural History
- Hotels near Chicago Riverwalk
- Hotels near Cloud Gate
- Hotels near Lollapalooza
- Hotels near Millennium Park
- Hotels near Michigan Avenue
- Hotels near McCormick Place
- The Loop Hotels
- Hotels near Adler Planetarium and Astronomy Museum
- Theatre District Hotels
- Fulton Market Hotels
- Cheap Hotels in Central Chicago
- Luxury Hotels in Central Chicago
- Boutique Hotels in Chicago
- Family Hotels in Chicago
- Hotels with Parking in Chicago
- Spa Hotels in Chicago
- Beach Hotels in Chicago
- Hotels with Pool in Chicago
- All Inclusive Hotels in Chicago
- Cheap Hotels in Chicago
- Luxury Hotels in Chicago
- Lgbt Welcoming Hotels in Gold Coast
- Lgbt Welcoming Hotels in Printers Row
- Lgbt Welcoming Hotels in Magnificent Mile
- Family Hotels in Magnificent Mile
- Cheap Hotels in Downtown Chicago
- Luxury Hotels in Downtown Chicago
- Romantic Hotels in Downtown Chicago
- Lgbt Welcoming Hotels in Downtown Chicago
- Beach Hotels in Downtown Chicago
- Family Hotels in Downtown Chicago
- Hotels with Parking in Downtown Chicago
- Wyndham Hotels in Chicago
- Accor Hotels in Chicago
- Nikko Hotels in Chicago
- Affinia Hotels in Chicago
- Kimpton Hotels in Downtown Chicago
- Grant Park
- Pritzker Pavilion
- Art Institute of Chicago
- Bridgeport Art Center
- Downtown Chicago Holidays
- Willis Tower
- Chicago Water Tower
- Copernicus Statue
- Merchandise Mart
- Mccormick Place
- Broadway Playhouse
- Cloud Gate
- Athenaeum Theatre
- Oak Street Beach
- Field Museum of Natural History
- Adler Planetarium and Astronomy Museum
- Supreme Life Building
- Ohio Street Beach
- Crown Fountain
- Buckingham Fountain
- Navy Pier
- Harold Washington Library Center
- Lincoln Park Zoo
- Water Tower Place
- Millennium Park
- Richard J. Daley Center
- Wintrust Arena
- Tribune Tower
- Chicago Board of Trade Building
- Gold Coast Holidays
- Adults Only Holiday Packages Central Chicago
- Visit Downtown Chicago
- Visit Prairie District
- Visit Chicago
- Visit The Loop
- Visit West Loop
- Suv Car Hire in Chicago
- Thrifty Car Rental Rental Cars in Central Chicago
- Avis Rental Cars in Chicago
- Fox Rental Cars Rental Cars in Chicago
- Thrifty Car Rental Rental Cars in Chicago
- Car hire near Chicago Museum Campus
- Car hire near Chicago
- Car hire near Magnificent Mile
- Car hire near The Loop
- Car hire near Downtown Chicago
- Car hire near Gold Coast
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
