Romantic Hotels & Resorts in Chicago from AU$241

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Check availability on Chicago Romantic Hotels

Best Chicago Romantic Hotels

The Chicago Hotel Collection - Magnificent Mile
Rooftop terrace

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.4 out of 10, Good, (1158)
"Very enjoyable stay"
The Chicago Hotel Collection - Magnificent Mile
Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2080)
"Best hotel "
The price is AU$338
includes taxes & fees
1 Sept - 2 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton
The Chicago Hotel Collection Ambassador Gold Coast
Terrace/patio

The Chicago Hotel Collection Ambassador Gold Coast

4.0 star property
8.2 out of 10, Very good, (1078)
"Great place to stay, would definitely recommend and stay here again "
The price is AU$274
includes taxes & fees
21 Aug - 22 Aug
The Chicago Hotel Collection Ambassador Gold Coast
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (8982)
"Great place to stay."
The price is AU$241
includes taxes & fees
1 Sept - 2 Sept
Congress Plaza Hotel
Swissotel - Chicago
Reception

Swissotel - Chicago

4.5 star property
9.0 out of 10, Wonderful, (2594)
"Great experience with staff, room and overall stay! "
The price is AU$330
includes taxes & fees
1 Sept - 2 Sept
Swissotel - Chicago
The Royal Sonesta Chicago Downtown
Exterior

The Royal Sonesta Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (2824)
"Staff were great and nice clean hotel. "
The price is AU$353
includes taxes & fees
1 Sept - 2 Sept
The Royal Sonesta Chicago Downtown
LondonHouse Chicago, Curio Collection by Hilton
Lobby

LondonHouse Chicago, Curio Collection by Hilton

4.5 star property
9.4 out of 10, Exceptional, (3334)
"Great place to stay"
The price is AU$348
includes taxes & fees
21 Aug - 22 Aug
LondonHouse Chicago, Curio Collection by Hilton
Hotel Saint Clair- Magnificent Mile
Restaurant

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (1703)
"We loved the price and location of this hotel. "
Hotel Saint Clair- Magnificent Mile
Hilton Chicago/Magnificent Mile Suites
Ballroom

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2624)
"Great location and hotel!"
The price is AU$258
includes taxes & fees
24 Aug - 25 Aug
Hilton Chicago/Magnificent Mile Suites
The Westin Michigan Avenue Chicago
View from room

The Westin Michigan Avenue Chicago

4.5 star property
8.8 out of 10, Excellent, (1007)
"Very nice place to stay great location"
The price is AU$291
includes taxes & fees
1 Sept - 2 Sept
The Westin Michigan Avenue Chicago
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.

Top Chicago Hotel Reviews

The Wade

The Wade

10/10 Excellent
"Loved staying at this hotel! This was our second time and we enjoyed it. Super easy to get everywhere and can walk downtown. Would definitely stay here again"
Jacqueline 3-night trip
Posted 23 hours ago
The Wade

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 want to soak in a hot tub or enjoy a candlelit dinner, there are 2 hotels and other accommodations in Chicago.
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. Another good option for your romantic getaway is A5 Luxurious Garden Unit Near Chicago.
How many romantic hotels should we expect to find in Chicago?
Expedia has 72 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 Michigan Avenue, 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.