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
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$335 per night from 17 Jan to 18 Jan
NZ$335
17 Jan - 18 Jan
includes taxes & fees
8.4/10 Very Good! (2,230 reviews)
Room was very clean and staff was great
Reviewed on 6 Jan 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$334 per night from 17 Jan to 18 Jan
NZ$334
17 Jan - 18 Jan
includes taxes & fees
8.4/10 Very Good! (2,494 reviews)
I paid for a king room and had that for the first half of my stay, but something went wrong with the water heater for the floor(?). It wasn't explained well to us, but we were moved into another room on a higher level which I assumed would have been similar but it was much smaller and had a queen ...
Reviewed on 5 Jan 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$182 per night from 18 Jan to 19 Jan
NZ$182
18 Jan - 19 Jan
includes taxes & fees
8.8/10 Excellent! (3,668 reviews)
Great hotel!
Reviewed on 5 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.
Navy Pier
One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.
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.
What to do in Chicago
Skydeck - Willis Tower Admission
NZ$76
per adult
100% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
NZ$42
per adult
88% of travellers recommend
Chicago Crime and Mob Bus Tour
NZ$84
per adult
92% of travellers recommend
Explore a world of travel with Expedia
- Cottages in Rush Street
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- Holiday Homes in Central Chicago
- Apartments in Jackson Station
- 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.
