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Check availability on Chicago Romantic Hotels

Our top choices for Chicago romantic hotels

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, (2258)
"This place was amazing !"
United States
Jayla Danyell
The price is 2.439.645 ₫
3.760.401 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
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, (2956)
"Great location and great staff!!"
United States
lynne
The price is 2.130.867 ₫
2.501.423 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Aloft Chicago Mag Mile
View from room
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3476)
"Great place to stay "
United States
RaShawna
The price is 2.135.602 ₫
2.506.984 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Hilton Chicago/Magnificent Mile Suites
Reception hall
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3149)
"Great location "
United States
Christian
The price is 2.274.826 ₫
2.670.419 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Eurostars Magnificent Mile
2 bars/lounges
Hyatt Regency Chicago

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3391)
"I always love staying at this place when I visit"
Canada
William
The price is 3.577.752 ₫
4.972.034 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Hyatt Regency Chicago
Indoor wedding
Swissotel - Chicago

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3010)
"Very beautiful place to stay"
United States
FaithBrenda
The price is 2.998.472 ₫
4.291.987 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
Swissotel - Chicago
Exterior
Warwick Allerton - Chicago

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (3008)
"Enjoyed this hotel stay. "
United States
Kimberly
The price is 1.662.602 ₫
2.723.563 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Warwick Allerton - Chicago
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, (2742)
"Clean room and friendly staff, overall good stay "
United States
eesaa saalik
The price is 2.043.130 ₫
3.171.328 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Lobby
Congress Plaza Hotel

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (9646)
"Great hotel and staff. "
Canada
Dane
The price is 3.604.177 ₫
4.230.945 ₫ total
includes taxes & fees
30 Dec - 31 Dec
Congress Plaza Hotel
View from property
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1594)
"Great stay!!"
United States
Adrian
The price is 2.571.509 ₫
3.018.695 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Courtyard by Marriott Chicago 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 Chicago Hotel Reviews

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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.
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 Michigan Avenue, Wrigley Field or Soldier 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.