Countryside Holidays
Photo by Monica Ferro
- 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
Countryside Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Aloft Chicago Downtown River North
Downtown Chicago
Price was S$6,248, price is now S$6,036 per person
S$6,036
per person
3 Feb - 8 Feb
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,159 reviews)
Enjoyed my stay . They treated my doggy as he was at home :)
Reviewed on 18 Dec, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was S$7,531, price is now S$6,782 per person
S$6,782
per person
3 Feb - 8 Feb
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Excellent stay.
Loved everything about this hotel. Definitely coming back.
Reviewed on 18 Dec, 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was S$6,257, price is now S$6,047 per person
S$6,047
per person
3 Feb - 8 Feb
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Clean room, beautiful hotel, location is great walking distance to everything. My only complaint was the pillows but that’s just an opinion. I’d stay here again!
Reviewed on 17 Dec, 2025
Top hotels in Countryside
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 12 Jan to 13 Jan
S$135
12 Jan - 13 Jan, 2026
includes taxes & fees
8.8/10 Excellent! (3,482 reviews)
Room was clean
Reviewed on 14 Dec, 2025
Silversmith Hotel Chicago Downtown
10 S Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$162 per night from 4 Jan to 5 Jan
S$162
4 Jan - 5 Jan, 2026
includes taxes & fees
9.2/10 Wonderful! (2,130 reviews)
This hotel was great. In a perfect spot for walking the city and taking in all the sights. We had 3 of us in our group and we got the 1br with 2 queens beds and a pullout couch and it was perfect. The bar was fun and everyone we met in the staff were so friendly and helpful with suggestions on places ...
Reviewed on 16 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$126 per night from 21 Dec to 22 Dec
S$126
21 Dec - 22 Dec
includes taxes & fees
8.6/10 Excellent! (1,989 reviews)
Very clean and the staff was wonderful!
Reviewed on 13 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
4.5/5(40 reviews)
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
4.5/5(36 reviews)
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
4/5(44 reviews)
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 Countryside
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 Forest View
- Motel 6 Hotels in Bellwood
- Hotels with smoking rooms in Bridgeview
- Bridgeview Hotels
- Broadview Hotels
- Burr Ridge Hotels
- Cicero Hotels
- Clarendon Hills Hotels
- Gay friendly Hotels in Clearing
- Hotels with Entertainment in Countryside
- Countryside Hotels
- Darien Hotels
- Downers Grove Hotels
- Apartments in Forest View
- Forest View Hotels
- Hotels near Galloping Ghost
- Hickory Hills Hotels
- Hillside Hotels
- Hometown Hotels
- Marriott Hotels & Resorts in Justice
- La Grange Hotels
- Lemont Hotels
- Little Village Hotels
- Lombard Hotels
- Maywood Hotels
- Condo Rentals in Melrose Park Bellwood Station
- Hotels near Midway Intl.
- North Riverside Hotels
- Oak Brook Hotels
- Casino Hotels in Oak Lawn
- Oak Lawn Hotels
- Palisades Hotels
- Palos Park Hotels
- River Forest Hotels
- Riverside Hotels
- Summit Hotels
- Western Springs Hotels
- Condo Rentals in Westmont
- Westmont Hotels
- Willowbrook Hotels
- Worth Hotels
- Flights to Hillside
- Flights to Hometown
- Flights to Indian Head Park
- Flights from Downers Grove
- Flights from Mosinee (CWA) to Chicago (MDW)
- 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 Seoul (ICN) to Chicago (MDW)
- Flights from Indianapolis (IND) to Chicago (MDW)
- Flights from Las Vegas (LAS) to Chicago (MDW)
- Flights from Los Angeles (LAX) to Chicago (MDW)
- Flights from Minneapolis (MSP) to Chicago (MDW)
- Flights from Portland (PDX) to Chicago (MDW)
- Flights from Rochester (ROC) to Chicago (MDW)
- Flights from San Diego (SAN) to Chicago (MDW)
- Flights from South Bend (SBN) to Chicago (MDW)
- Flights from San Francisco (SFO) to Chicago (MDW)
- Flights from Singapore (SIN) to Chicago (MDW)
- Flights from Vancouver (YVR) to Chicago (MDW)
- Flights from Toronto (YYZ) to Chicago (MDW)
- Apollo Theater Chicago
- Art Institute of Chicago
- Visit Bellwood
- Blue Island Holidays
- Buckingham Fountain
- Centennial Beach
- Centennial Park Aquatic Center
- Visit Bedford Park
- Chicago Museum Campus Holidays
- Visit West Lawn
- Cicero Holidays
- Cna Center
- Visit Crestwood
- Downers Grove Holidays
- Elmhurst Holidays
- Frank Lloyd Wright Historic District
- Goose Island Holidays
- Grant Park
- Harvey Public Library
- Mccormick Place
- Melrose Park Holidays
- Visit Melrose Park
- Merchandise Mart
- Millennium Park
- Morton Arboretum
- Oakbrook Center Mall
- Palos Hills Holidays
- Pritzker Pavilion
- Shops at North Bridge
- Soldier Field
- Stone Park Holidays
- University of Illinois Chicago
- Walt Disney House
- 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.
