Find Romantic Hotels in Westchester, IL from $127

Start date: Check-in selected.
To Date
End date: Check-out

Check availability on Westchester Romantic Hotels

Top Westchester Romantic Hotels

Warwick Allerton - Chicago
Lobby sitting area
Warwick Allerton - Chicago
4.0 star property
8.4 out of 10, Very Good, (2920)
"Great location, friendly staff."
$113 nightly
The price is $133
Nov 3 - Nov 4
Total with taxes and fees
Warwick Allerton - Chicago
Millennium Knickerbocker Chicago
Lobby
Millennium Knickerbocker Chicago
4.0 star property
8.6 out of 10, Excellent, (1992)
"We have stayed here several times and love the hotel and location."
$119 nightly
The price is $140
Nov 12 - Nov 13
Total with taxes and fees
Millennium Knickerbocker Chicago
Aloft Chicago Mag Mile
Cocktail bar
Aloft Chicago Mag Mile
3.0 star property
8.6 out of 10, Excellent, (2861)
"Had a great stay!"
$138 nightly
The price is $162
Nov 9 - Nov 10
Total with taxes and fees
Aloft Chicago Mag Mile
Hilton Chicago/Magnificent Mile Suites
Ballroom
Hilton Chicago/Magnificent Mile Suites
3.5 star property
8.8 out of 10, Excellent, (3089)
"Our stay was great"
$144 nightly
The price is $169
Nov 9 - Nov 10
Total with taxes and fees
Hilton Chicago/Magnificent Mile Suites
Eurostars Magnificent Mile
Reception
Eurostars Magnificent Mile
4.0 star property
8.8 out of 10, Excellent, (3079)
"Very nice location and everything was a 10/10"
$108 nightly
The price is $127
Nov 12 - Nov 13
Total with taxes and fees
Eurostars Magnificent Mile
Silversmith Hotel Chicago Downtown
Lobby
Silversmith Hotel Chicago Downtown
4.0 star property
9.4 out of 10, Exceptional, (2016)
"Great place to stay "
$170 nightly
The price is $199
Nov 2 - Nov 3
Total with taxes and fees
Silversmith Hotel Chicago Downtown
Congress Plaza Hotel
Banquet hall
Congress Plaza Hotel
3.5 star property
8.0 out of 10, Very Good, (9398)
"Beautiful hotel!"
$145 nightly
The price is $170
Nov 2 - Nov 3
Total with taxes and fees
Congress Plaza Hotel
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, (1174)
"Room and breakfast fantastic!"
$165 nightly
The price is $194
Oct 26 - Oct 27
Total with taxes and fees
The Chicago Hotel Collection Ambassador Gold Coast
The Godfrey Hotel Chicago
American cuisine, alfresco dining
The Godfrey Hotel Chicago
4.5 star property
8.6 out of 10, Excellent, (1898)
"Attentive staff, great location "
$143 nightly
The price is $168
Nov 3 - Nov 4
Total with taxes and fees
The Godfrey Hotel Chicago
Virgin Hotels Chicago
Rooftop terrace
Virgin Hotels Chicago
4.5 star property
9.2 out of 10, Wonderful, (1382)
"Great place to stay near everything."
$198 nightly
The price is $232
Nov 13 - Nov 14
Total with taxes and fees
Virgin Hotels 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.
View all properties

Top Westchester Hotel Reviews

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

10/10 Excellent
"Excellent location for visiting Chicago, near major attractions, walking distance to mig mile and Chicago river. Subway station is beside the hotel. Many restaurants are around. Hotel is a little old but condition is good and the price is reasonable. Staffs are very friendly. "
Xiaoyi 4-night trip
Posted 6 hours ago
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Frequently asked questions

Searching for romantic hotels in Westchester?
Are you in need of a romantic vacation? Our guests also enjoy Westchester for its restaurants and shopping. If you want to get out and explore the larger area, you might head to Wrigley Field, Michigan Avenue, or Navy Pier. If you're interested in staying close to a particular destination, you can sort properties by neighborhood 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 Westchester?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Westchester: The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Westchester are January, November, February, and December, with each month seeing an average of 5 inches of snowfall.
What is there to do in Westchester?
There's nothing better than wandering around a new destination with your sweetheart, so consider taking time to discover all that Westchester has to offer. If you and your partner are interested in sampling the area's cuisine, you'll enjoy Westchester for its restaurants. There's plenty to see in the greater Chicago area, so you might plan to visit Wrigley Field, Michigan Avenue, or Navy Pier.
What's the best way to get to Westchester and around town during my romantic getaway?
This information about transportation options in Westchester might help your romantic trip get off to a smooth start: The closest major airport is Chicago Midway Airport (MDW), located 8.4 mi (13.4 km) from the city center. If you'd like to venture out around the area, consider renting a car to take in more sights.

Explore a world of travel with Expedia