A river with a yellow boat, surrounded by tall buildings and a bridge.

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Check availability on Chicago Romantic Hotels

Tonight
26 Oct - 27 Oct
Tomorrow
27 Oct - 28 Oct
This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Top Chicago Hotel Reviews

Hilton Chicago

Hilton Chicago

8/10 Good
"Everyone so nice but long lines to check in."
Elvira 1-night trip
Posted less than an hour ago
Hilton Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"A wonderful place with a prime location in an exclusive, central neighborhood. The hotel is beautiful and spotless, the food is delicious, and the bed is super comfortable! You can tell how much they prioritize cleanliness throughout the entire stay."
Marisara 2-night trip
Posted less than an hour ago
The Chicago Hotel Collection Ambassador Gold Coast
The Wade

The Wade

10/10 Excellent
"Great stay"
Roena 3-night trip
Posted 2 hours ago
The Wade
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

8/10 Good
"First the good: the location is great, right on the river and easily walkable to the Loop of the Magnificent Mile, etc. I arrived early and asked to check my bag, but my room was ready, which was nice. Somehow I got a fabulous upgrade to a comfortable spacious corner room on the 38th floor with the most spectacular views (views plural). When I returned later to rest before dinner, I couldn’t stop looking out the windows—what a show at sunset! The bed was very comfortable, although really really high off the ground. Everything seemed clean. Now the not-so-good: lighting was very sparse in the room—half the room had no lighting at all. No place to charge devices—hello, this is 2026. I had a little trouble with the temperature and there was no way to call downstairs—everything has to be handled in the app. So do stay here, but bring a charging station to plug into the wall—which is far from the bed."
LINDA 1-night trip
Posted 6 hours ago
The Royal Sonesta Chicago Downtown
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent
"Great hotel in a great location. Highly recommended"
Elio 2-night trip
Posted 14 hours ago
LondonHouse Chicago, Curio Collection by Hilton
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

10/10 Excellent
"Great spot!"
Sean 3-night trip
Posted 15 hours ago
Sports Illustrated Resorts Chicago
Freehand Chicago

Freehand Chicago

8/10 Good
"Good value"
Francis 3-night trip
Posted 18 hours ago
Freehand Chicago
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"I really enjoyed my stay here! One of the first things I noticed was how clean and well-kept everything was, which made me feel comfortable right away. The staff was amazing, always friendly, welcoming, and willing to help with anything I needed. I also really appreciated how convenient the location was. It made getting around so much easier. It's always nice to stay somewhere that feels comfortable and where you're treated well. I had a great experience overall and would definitely stay here again. Highly recommend!"
Jorje 1-night trip
Posted 19 hours ago
Fairmont Chicago at Millennium Park

Frequently asked questions

Searching for romantic hotels in Chicago?
Are you in need of a romantic getaway? Couples choose Chicago for its popular theatre scene and scenic landscape. If you want to spend a romantic day sharing a bottle of wine with your love, you might plan a visit to Lynfred Winery, Valentino Vineyards or Broken Earth Winery. Whether you and your partner are looking for some relaxing time away or you're hoping to stay near top romantic sights, you can choose from 15 hotels and other accommodation options in Chicago for the ideal romantic holiday.
What's the best hotel for couples in Chicago?
Chicago Guest House Wrigleyville is a favourite hotel for couples, and features free WiFi and free parking.
How many romantic hotels should we expect to find in Chicago?
Expedia has 15 romantic Chicago hotels for you to get cosy in.
When is the best time of year for a romantic getaway to Chicago?
If you're looking forward to lots of outings with your partner, take a look at these details about year-round temperatures in Chicago: The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of -1°C. Average annual precipitation for Chicago is 1260 mm.
What is there to do in Chicago?
There's nothing better than wandering around a new destination with your sweetheart, so consider checking out all there is to see and do in Chicago. If you're hoping to experience some of the local culture, you'll love Chicago for its popular theatre scene, stunning architecture and top museums. A visit to Soldier Field, Navy Pier or Wrigley Field might be just the ticket when you're checking out the sights.
What's the best way to get to Chicago and around town during my romantic getaway?
This information about transportation options in Chicago might help your romantic trip go off without a hitch: Make your way to Chicago with a flight to Chicago Midway Airport (MDW), which is the closest major airport located 8.6 mi (13.9 km) away. You can access metro transport at Monroe Station (Red Line), Monroe Station (Blue Line) and Adams-Wabash Station.

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