Countryside Holidays
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Countryside Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was S$2,695, price is now S$2,071 per person
S$2,071
per person
2 May - 8 May
found 1 day ago
Return flight included
Singapore (SIN) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
The hotel was nice , and clean. The guy at the front desk was super nice. However , the rooms are small, the shower water splashes over on to floor so extra towels are needed for the bathroom floor, and every vending machine was either jammed and or out of water.
Reviewed on 17 Mar, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was S$3,606, price is now S$2,369 per person
S$2,369
per person
2 May - 8 May
found 1 day ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
The property was absolutely stunning and the staff was great.
Reviewed on 18 Mar, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was S$3,003, price is now S$2,311 per person
S$2,311
per person
2 May - 8 May
found 1 day ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
The staff was super helpful and very welcoming. The room had an amazing view for us, beings it was our first time being in Chicago. It’s was so close to everything we wanted to visit and super convenient. I will most definitely stay at this hotel again for future stays in the city.!! Thank you so much for taking pride in your establishment, and your employees, as both we’re definitely deserving of a 5 star rating and review.!
Reviewed on 17 Mar, 2026
Hilton Chicago O'Hare Airport
O'Hare
Price was S$2,889, price is now S$2,292 per person
S$2,292
per person
2 May - 8 May
found 1 day ago
Return flight included
Singapore (SIN) to Chicago (ORD)
8.4/10 Very Good! (2,231 reviews)
Everything went pretty well. Glad we choose to stay there.
Reviewed on 15 Mar, 2026
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
Price was S$2,926, price is now S$2,396 per person
S$2,396
per person
2 May - 8 May
found 1 day ago
Return flight included
Singapore (SIN) to Chicago (ORD)
8.6/10 Excellent! (4,398 reviews)
We stay at this hotel each time we travel to downtown Chicago and the price, cleanliness, location and overall experience is always wonderful.
Reviewed on 17 Mar, 2026
Top hotels in Countryside
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$189 per night from 20 Mar to 21 Mar
S$189
20 Mar - 21 Mar
includes taxes & fees
8/10 Very Good! (9,971 reviews)
Excellent location!! Very friendly staff that are so appreciative when given a tip!
Reviewed on 18 Mar, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$234 per night from 24 Mar to 25 Mar
S$234
24 Mar - 25 Mar
includes taxes & fees
9.4/10 Exceptional! (3,562 reviews)
Not what we expected. The roof top was close. The bar downstairs was super pack, couldn’t even watch Tv because the tv didn’t work, We had to pay everything even for water. Elevators took forever.
Reviewed on 18 Mar, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$195 per night from 24 Mar to 25 Mar
S$195
24 Mar - 25 Mar
includes taxes & fees
8.6/10 Excellent! (5,742 reviews)
Good room lower floor was a little close to the street and a little loud but it’s Chicago so to be expected. Breakfast was good and the room was clean.
Reviewed on 18 Mar, 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.
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.
Millennium Park
4.5/5(147 reviews)
One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.
What to do in Countryside
Skydeck - Willis Tower Admission
S$56
per adult
98% of travellers recommend
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- Flights to Hillside
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- 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.
