Find Romantic Hotels in Countryside from S$130

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Check availability on Countryside Romantic Hotels

Tonight
23 Dec - 24 Dec
Tomorrow
24 Dec - 25 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Countryside romantic hotels

Lobby
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2982)
"Great place to stay"
United States
Elisha
The price is S$130
includes taxes & fees
22 Jan - 23 Jan, 2026
Aloft Chicago Mag Mile
Exterior
Warwick Allerton - Chicago

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (3004)
"Enjoyed this hotel stay. "
United States
Kimberly
The price is S$158
includes taxes & fees
28 Dec - 29 Dec
Warwick Allerton - Chicago
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2284)
"Great staff and restaurants!!"
United States
Abigale
The price is S$173
includes taxes & fees
20 Jan - 21 Jan, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Exterior
Hilton Chicago

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2410)
"The room was clean and the staff was outstanding. "
United States
Albert
The price is S$210
includes taxes & fees
30 Dec - 31 Dec
Hilton Chicago
2 bars/lounges
Hyatt Regency Chicago

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3416)
"The Hotel was amazing great location "
United States
Donnisha
The price is S$256
includes taxes & fees
20 Jan - 21 Jan, 2026
Hyatt Regency Chicago
55-inch LCD TV with cable channels, TV, pay films
L7 Chicago by LOTTE

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3428)
"Very good stay "
United States
david
The price is S$209
includes taxes & fees
28 Dec - 29 Dec
L7 Chicago by LOTTE
Exterior
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (2760)
"Excellent place to stay "
United States
Teniesha
The price is S$165
includes taxes & fees
6 Jan - 7 Jan, 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Ballroom
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3181)
"Staff, location, views and rooms were amazing!!"
United States
Gabriela Michelle Riveiro
The price is S$213
includes taxes & fees
21 Jan - 22 Jan, 2026
The Royal Sonesta Chicago Downtown
Lobby
Congress Plaza Hotel

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (9697)
"Wonderful stay!"
United States
Zach
The price is S$312
includes taxes & fees
31 Dec - 1 Jan, 2026
Congress Plaza Hotel
Reception hall
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3156)
"Amazing stay very clean and beautiful views "
United States
Deigo
The price is S$142
includes taxes & fees
22 Jan - 23 Jan, 2026
Eurostars Magnificent Mile
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.
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Top Countryside Hotel Reviews

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

10/10 Excellent
"The staff were wonderful! The only thing I missed in the room was a desk."
Lillian 4-night trip
Posted 16 hours ago
Silversmith Hotel Chicago Downtown

Frequently asked questions

Searching for romantic hotels in Countryside?
Are you looking for a romantic holiday? Our guests also enjoy Countryside for its restaurants and shopping. If you want to see some sights and attractions in the greater Countryside area, you might head to Michigan Avenue, Wrigley Field or United Center. If you'd like to stay close to a particular destination, you can sort properties by neighbourhood or distance to top sights, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Countryside?
If you're hoping to get lost in the rain on your romantic getaway, take a look at these details about year-round temperatures in Countryside: The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of -1°C. Average annual precipitation for Countryside is 1236 mm.
What is there to do in Countryside?
There's nothing better than wandering around a new destination with your sweetheart, so consider taking time to discover all that Countryside has to offer. If you and your partner are interested in sampling the area's cuisine, you'll love Countryside for its array of dining options. There's plenty to see in the greater Chicago area, so you might plan to visit Michigan Avenue, Wrigley Field or United Center.
What's the best way to get to Countryside and around town during my romantic getaway?
This information about transportation options in Countryside might help your romantic trip go off without a hitch: To get to Countryside, you can fly into Chicago Midway Airport (MDW), which is the closest major airport, located 7.3 mi (11.8 km) from the city centre. If you'd like to venture out around the area, you may want a rental car for your journey.

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