Crestwood Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$134 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
Top hotels in Crestwood
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$135 per night from 5 Jan to 6 Jan
S$135
5 Jan - 6 Jan, 2026
includes taxes & fees
8.8/10 Excellent! (3,522 reviews)
Clean room, few dust spots, warm and cozy stay
Reviewed on 20 Dec, 2025
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$230 per night from 2 Jan to 3 Jan
S$230
2 Jan - 3 Jan, 2026
includes taxes & fees
8.4/10 Very Good! (2,168 reviews)
Decent room and the staff at the front desk and restaurant were friendly and helpful. The front desk area is cramped and confusing (i.e.) once you get your key card from check-in, it is so tight in that area that that it’s unclear how you get out of the area without pushing past the people in line ...
Reviewed on 22 Dec, 2025
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$123 per night from 7 Jan to 8 Jan
S$123
7 Jan - 8 Jan, 2026
includes taxes & fees
8.6/10 Excellent! (1,999 reviews)
good
Reviewed on 21 Dec, 2025
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.
Popular places to visit
Wrigley Field
Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.
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.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
What to do in Crestwood
Wendella's 90-min Chicago River Architecture Tour
S$52
per adult
94% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
S$263
per adult
80% of travellers recommend
Explore a world of travel with Expedia
- 4 Star Hotels in Hazel Crest
- 4 Star Hotels in Tinley Park
- 5 Star Hotels in Pullman
- Alsip Hotels
- Blue Island Hotels
- Hotels with smoking rooms in Bridgeview
- Bridgeview Hotels
- Calumet Park Hotels
- B&B in Chicago 83rd Street Station
- Gay friendly Hotels in Clearing
- Cookes Subdivision Hotels
- Country Club Hills Hotels
- Hotels with Entertainment in Countryside
- Crestwood Hotels
- Dolton Hotels
- Evergreen Park Hotels
- Red Roof Inn Hotels in Far Southwest Side
- Hotels near Harvey 147th Street-Sibley Boulevard Station
- Hazel Crest Hotels
- Hickory Hills Hotels
- Hometown Hotels
- Marriott Hotels & Resorts in Justice
- Markham Hotels
- Resorts in Markham
- Mount Greenwood Hotels
- Oak Forest Hotels
- Casino Hotels in Oak Lawn
- Oak Lawn Hotels
- Orland Park Hotels
- Palos Park Hotels
- Phoenix Hotels
- Hostels in Riverdale
- Gay friendly Hotels in Riverdale
- Riverdale Hotels
- Roseland Hotels
- Sonesta Hotel in South Suburbs
- Hotels with smoking rooms in Tinley Park
- Tinley Park Hotels
- West Pullman Hotels
- Worth Hotels
- Flights to Blue Island
- Flights to Evergreen Park
- Flights to Hometown
- Flights to Markham
- Flights from Hazel Crest
- Flights from Oak Forest
- Flights from Dallas (DFW) to Chicago (MDW)
- Flights from Newark Liberty Intl. Airport (EWR) to Chicago (MDW)
- Flights from Gainesville (GNV) to Chicago (MDW)
- Flights from Indianapolis (IND) to Chicago (MDW)
- Flights from Los Angeles (LAX) to Chicago (MDW)
- Flights from Rochester (ROC) to Chicago (MDW)
- Flights from Singapore (SIN) to Chicago (MDW)
- Flights from Vancouver (YVR) to Chicago (MDW)
- Flights from Toronto (YYZ) to Chicago (MDW)
- Aon Center
- Art Institute of Chicago
- Blue Island Holidays
- Visit Blue Island
- Burnham Park
- Centennial Park Aquatic Center
- Visit Cookes Subdivision
- Visit Morgan Park
- Chicago Museum Campus Holidays
- Visit West Lawn
- Chicago Holidays
- Cicero Holidays
- Cloud Gate
- Cna Center
- Countryside Holidays
- Visit Crestwood
- Visit Dolton
- Downers Grove Holidays
- Downtown Chicago Holidays
- Frank Lloyd Wright Historic District
- Gold Coast Holidays
- Grant Park
- Harvey Public Library
- Mccormick Place
- Melrose Park Holidays
- Millennium Park
- Oakbrook Center Mall
- Visit Orland Park
- Palos Hills Holidays
- Pritzker Pavilion
- Schrum Holidays
- Shops at North Bridge
- Soldier Field
- Visit Orland Hills
- Visit Tinley Park
- University of Illinois Chicago
- West Town Holidays
- Willis Tower
- Willowbrook Community Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
