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Check availability on Near West Side Romantic Hotels

Our top choices for Near West Side romantic hotels

Exterior
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1753)
"Lovely hotel."
United States
Cedrick
The price is 2.349.567 ₫
2.758.156 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Crowne Plaza Chicago West Loop by IHG
Exterior detail
The Emily Hotel

The Emily Hotel

The Emily Hotel
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1277)
"great hotel! amazing staff and very clean!"
United States
Marielle
The price is 8.347.525 ₫
9.799.161 ₫ total
includes taxes & fees
13 Dec - 14 Dec
The Emily Hotel
Staircase
The Publishing House B&B

The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (189)
"Wonderful staff, beautiful hotel and great breakfast!"
United States
Veronica
The price is 5.323.060 ₫
6.009.203 ₫ total
includes taxes & fees
18 Dec - 19 Dec
The Publishing House B&B
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, (2950)
"Great location and great staff!!"
United States
lynne
The price is 2.134.917 ₫
2.506.181 ₫ total
includes taxes & fees
4 Jan - 5 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 1.665.762 ₫
2.728.740 ₫ total
includes taxes & fees
23 Dec - 24 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
8.4 out of 10, Very good, (2739)
"Great food clean room friendly staff"
United States
MARINA
The price is 2.066.389 ₫
3.199.311 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
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, (2257)
"This place was amazing !"
United States
Jayla Danyell
The price is 2.528.691 ₫
3.865.887 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Sable at Navy Pier Chicago, Curio Collection by Hilton
Reception hall
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3144)
"Amazing and will be staying again!"
United States
Angie
The price is 2.278.368 ₫
2.674.575 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Eurostars Magnificent Mile
Reception
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2135)
"Loved and enjoyed our stay"
United States
Luis
The price is 2.917.720 ₫
4.084.036 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Palmer House a Hilton Hotel
Lobby
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2112)
"Great hotel. Very affordable for such a perfect location."
United States
Nicholas
Silversmith Hotel Chicago Downtown
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 Near West Side Hotel Reviews

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Frequently asked questions

Searching for romantic hotels in Near West Side?
If you and your partner need some romantic time away, we'd like to help you plan for it. Our guests also enjoy Near West Side for its live music, theatre scene and shopping. If you want to explore the area, you might head to United Center, Credit Union 1 Arena or Milwaukee Avenue. If you'd like to stay close to a certain attraction, you can sort properties by neighbourhood or distance to top landmarks, so you and your partner will get to see everything on your list.
What is there to do in Near West Side?
There's nothing better than wandering around a new place with your sweetheart, so consider checking out all that Near West Side has to offer. If you're hoping to see some of the area's cultural attractions, you'll enjoy Near West Side for its live music, theatre scene and shopping. You might consider a visit to United Center, Credit Union 1 Arena or Milwaukee Avenue.
What's the best way to get to Near West Side and around town during my romantic getaway?
These transportation options in Near West Side might help your romantic trip go off without a hitch: If you're looking to fly in, the closest major airport is iChicago Midway Airport (MDW), located 7.1 mi (11.5 km) away. Walk to nearby metro stations such as Polk Station (Pink Line), Racine Station and Illinois Medical District Station.