Chicago Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NT$5,067 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Find the Best Chicago Vacation Packages
Chicago Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$5,956 per night from Mar 13 to Mar 14
NT$5,956
NT$6,991 total
Mar 13 - Mar 14
includes taxes & fees
8/10 Very Good! (9,903 reviews)
The family suite was spacious!
Reviewed on 2026/2/17
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$3,109 per night from Mar 4 to Mar 5
NT$3,109
NT$4,534 total
Mar 4 - Mar 5
includes taxes & fees
9.2/10 Wonderful! (3,362 reviews)
Clean room, breakfast room staff friendly and efficient, check in and checkout fast. They accommodated my room location preferences and it was a quiet sleep. I like hard floors instead of carpet but the same vinyl flooring was used throughout which made the whole place feel like a hospital vs nice ...
Reviewed on 2026/2/17
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$4,344 per night from Feb 27 to Feb 28
NT$4,344
NT$6,019 total
Feb 27 - Feb 28
includes taxes & fees
8.4/10 Very Good! (2,638 reviews)
All of the staff we talked to were extremely kind and helpful. We had something sent to the room twice. Both times the items arrived within 10 minutes. The room, which we paid $99 (after tax) to upgrade to, had a really great view of the lake, Navy Pier and Museum Campus. The room was updated. Even ...
Reviewed on 2026/2/16
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
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Explore a world of travel with Expedia
- Hotels near Clinton Station
- Hotels near Grant Park
- Family Hotels in Chicago
- 5 Star Hotels in Magnificent Mile
- Hotels near Millennium Station
- Hotels with Hot Tubs in Downtown Chicago
- Hotels near DePaul University-Loop Campus
- Hotels near Quincy Metro Station
- 3 Star Hotels in Downtown Chicago
- All-Inclusive Hotel Hotels in Chicago
- Business Hotels in Chicago
- Hotels near UIC-Halsted Station
- Casino Hotels in Chicago
- Hotels with an Indoor Pool in South Loop
- Hotels near Monadnock Building
- Steigenberger Hotels in Chicago
- Hotels with Early Check-in in Chicago
- Boutique Hotels in Chicago
- Romantic Hotels in Downtown Chicago
- Adventure Hotels in Chicago
- Hilton Hotels in Downtown Chicago
- Hotels near Lollapalooza
- Hotels near Chicago Van Buren Street Station
- 4 Star Hotels in Magnificent Mile
- Hotels with smoking rooms in Downtown Chicago
- Luxury Hotels in Chicago
- Hostmark Hospitality Group Hotels in Chicago
- Chicago Hotels
- Family Hotels in The Loop
- Marriott Hotels & Resorts in Chicago
- Beach Hotels in Chicago
- Hotels with a Pool in Streeterville
- Hotels near Wintrust Arena
- Hotels with Free Parking in River North
- Hotel with a Concierge Hotels in Magnificent Mile
- Omni Hotels in Chicago
- B&B in Chicago Union Station
- Hotels near Chicago Union Station
- Hotels with an Indoor Pool in Chicago
- Winery Hotels in Chicago
- Hotels with Bars in Chicago
- Gay friendly Hotels in Downtown Chicago
- Nikko Hotels in Chicago
- Adults Only Resorts & in Chicago
- Resorts & Hotels with Spas in Chicago
- Gay friendly Hotels in West Loop
- Hotel Wedding Venues Hotels in Downtown Chicago
- Gay friendly Hotels in Chicago
- Affinia Hotels in Chicago
- 5 Star Hotels in Chicago
- Cabin Rentals in Chicago
- Hotels with WiFi in Downtown Chicago
- Hotels near Cermak-Chinatown Station
- Merchandise Mart
- Chicago Theatre
- Prentice Women's Hospital
- Willis Tower
- Art Institute of Chicago
- Chicago Children's Museum
- Water Tower Place
- Cooking & Hospitality Institute of Chicago
- Oak Street Beach
- Shops at North Bridge
- Crown Fountain
- Visit Greektown
- Northwestern Memorial Hospital
- Visit Chicago
- Buckingham Fountain
- Gold Coast Vacations
- Afrocentric Bookstore
- Navy Pier
- Chicago Riverwalk
- Museum of Contemporary Art Chicago
- 333 West Wacker Drive
- State Street
- Harold Washington Library Center
- Millennium Park
- Bridgehouse and Chicago River Museum
- Newberry Library
- The East Bank Club
- 311 S Wacker Dr
- Visit Downtown Chicago
- Grant Park
- Chicago City Hall
- Vietnam Veterans Memorial
- Film Row Cinema
- Firefly Rental Cars in The Loop
- Car rentals near Chicago
- Budget Rental Cars in Downtown Chicago
- Car rentals near University of Illinois Chicago
- Alamo Rent A Car Rental Cars in Chicago
- Car rentals near Water Tower Place
- Avis Rental Cars in The Loop
- Compact Car Rentals in Chicago
- Luxury Car Rentals in Chicago
- Ok Mobility Rental Cars in Chicago
- Economy Car Rentals in Chicago
- Mini Car Rentals in Chicago
- Car rentals near Streeterville
- Avis Rental Cars in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
