Find Romantic Hotels in Wicker Park, IL

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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Wicker Park Romantic Hotels

Our top choices for Wicker Park romantic hotels

3 bars/lounges, cocktail bar, rooftop bar, rooftop bar
The Robey, Chicago, a Member of Design Hotels

The Robey, Chicago, a Member of Design Hotels

The Robey, Chicago, a Member of Design Hotels
3.5 star property
West Town
9.2 out of 10, Wonderful, (1001)
"Good location, great staff!"
United States
Veronica
The price is AED 468
AED 640 total
includes taxes & fees
4 Jan - 5 January 2026
The Robey, Chicago, a Member of Design Hotels
Property entrance
Wicker Park Inn

Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (256)
"The Wicker Park Inn is clean, beautifully decorated, and the staff is friendly and helpful!"
United States
Elizabeth R
Wicker Park Inn
Premium bedding, pillowtop beds, desk, free WiFi
Ruby Room

Ruby Room

Ruby Room
2.5 star property
West Town
8.0 out of 10, Very Good, (656)
"Great location. Would stay again. "
United States
Wesley
The price is AED 469
AED 551 total
includes taxes & fees
15 Dec - 16 Dec
Ruby Room
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, (2961)
"Great location and great staff!!"
United States
lynne
The price is AED 290
AED 341 total
includes taxes & fees
14 Jan - 15 January 2026
Aloft Chicago Mag Mile
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, (2745)
"Clean room and friendly staff, overall good stay "
United States
eesaa saalik
The price is AED 282
AED 439 total
includes taxes & fees
11 Jan - 12 January 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Lobby sitting area
Warwick Allerton - Chicago

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (3013)
"Enjoyed this hotel stay. "
United States
Kimberly
The price is AED 291
AED 449 total
includes taxes & fees
21 Dec - 22 Dec
Warwick Allerton - Chicago
Ballroom
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, (2131)
"Loved and enjoyed our stay"
United States
Luis
The price is AED 407
AED 569 total
includes taxes & fees
21 Dec - 22 Dec
Palmer House a Hilton Hotel
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3154)
"Amazing stay very clean and beautiful views "
United States
Deigo
The price is AED 344
AED 404 total
includes taxes & fees
12 Jan - 13 January 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, (3395)
"I always love staying at this place when I visit"
Canada
William
The price is AED 499
AED 694 total
includes taxes & fees
28 Dec - 29 Dec
Hyatt Regency Chicago
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, (2261)
"This place was amazing !"
United States
Jayla Danyell
The price is AED 337
AED 521 total
includes taxes & fees
23 Dec - 24 Dec
Sable at Navy Pier Chicago, Curio Collection by Hilton
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 Wicker Park Hotel Reviews

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"Great staff"
Sara 2-night trip
Posted 5 hours ago
The Whitehall Hotel, BW Premier Collection

Explore a world of travel with Expedia

Frequently asked questions

Searching for romantic hotels in Wicker Park?
If you and your partner need a romantic escape, we've got just the ticket. Our guests also enjoy Wicker Park for its shopping, live music, and restaurants. If you'd like to explore some of the area's notable sights, you might make a stop by Milwaukee Avenue, Flat Iron Building, or Monique Meloche Gallery. If you're interested in staying close to a certain attraction, you can sort by neighborhood and proximity to top sights, so you'll be able to see everything on your list.
What is there to do in Wicker Park?
There's nothing better than wandering around a new place with your sweetheart, so consider taking time to discover all that Wicker Park has to offer. Couples looking for a little of everything will enjoy Wicker Park for its shopping, live music, and restaurants. You might think about stopping by Milwaukee Avenue, Flat Iron Building, or Monique Meloche Gallery while you're seeing the sights.
What's the best way to get to Wicker Park and around town during my romantic getaway?
These transportation options in Wicker Park might help your romantic trip get off to a smooth start: Make your way to Wicker Park with a flight to Chicago Midway Airport (MDW), which is the closest major airport located 8.9 mi (14.3 km) away. Local metro stations include Damen Station and Division Station.