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Find Romantic Hotels in Woodlawn, Chicago from CA $96

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Check availability on Woodlawn Romantic Hotels

Tonight
Aug 4 - Aug 5
Tomorrow
Aug 5 - Aug 6
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Top Woodlawn Romantic Hotels

We don't have any properties that match your exact search

Recommended hotels in Woodlawn

Best Motel By OYO Chicago I-90
Stairwell with a metal railing and large window featuring a decorative pattern.

Best Motel By OYO Chicago I-90

2.0 star property
3.2 out of 10, (33)
"Easy, safe parking "
The price is CA $96
CA $116 total
includes taxes & fees
Sep 3 - Sep 4
Best Motel By OYO Chicago I-90
Ameristar Casino Hotel East Chicago
Relax in a cozy lounge area with a fireplace, comfortable seating, and a vibrant abstract painting.

Ameristar Casino Hotel East Chicago

4.0 star property
8.4 out of 10, Very good, (1008)
"Very nice and the staff"
The price is CA $122
CA $151 total
includes taxes & fees
Aug 20 - Aug 21
Ameristar Casino Hotel East Chicago
Sable at Navy Pier Chicago, Curio Collection by Hilton
Relax in style with lounge chairs and bar stools amidst a scenic backdrop.

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2056)
"Beautiful property, will definitely stay there again."
The price is CA $246
CA $328 total
includes taxes & fees
Sep 1 - Sep 2
Sable at Navy Pier Chicago, Curio Collection by Hilton
The Wade
Enjoy a sea view from the large window, with a comfortable seating area and unique artwork on display.

The Wade

4.5 star property
8.2 out of 10, Very good, (1153)
"It was a very relaxing stay and amazing view!"
The price is CA $164
CA $193 total
includes taxes & fees
Sep 1 - Sep 2
The Wade
Swissotel - Chicago
Enjoy a panoramic city view from this stylish room, featuring a spacious dining area with a round table and six comfortable chairs.

Swissotel - Chicago

4.5 star property
8.8 out of 10, Excellent, (2548)
"Hotel is amazing "
The price is CA $272
CA $359 total
includes taxes & fees
Sep 1 - Sep 2
Swissotel - Chicago
Loews Chicago Hotel
Hotel entrance with a prominent sign and contemporary design.

Loews Chicago Hotel

4.5 star property
9.4 out of 10, Exceptional, (1514)
"This is a nice hotel in a great neighborhood. "
The price is CA $274
CA $366 total
includes taxes & fees
Sep 1 - Sep 2
Loews Chicago Hotel
DoubleTree by Hilton Chicago - Magnificent Mile
Relax by the pool surrounded by lounge chairs and umbrellas, taking in the city skyline views.

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1955)
"Very pleasant stay!"
The price is CA $219
CA $258 total
includes taxes & fees
Sep 1 - Sep 2
DoubleTree by Hilton Chicago - Magnificent Mile
Radisson Blu Aqua Hotel Chicago
Relax by the rectangular pool with marked lanes, surrounded by sun loungers and a seating area.

Radisson Blu Aqua Hotel Chicago

4.5 star property
8.4 out of 10, Very good, (1578)
"Lovely hotel and in the most convenient location"
The price is CA $254
CA $340 total
includes taxes & fees
Aug 17 - Aug 18
Radisson Blu Aqua Hotel Chicago
Fairmont Chicago at Millennium Park
Enjoy a meal in the kitchen with a large island and dining area, offering a view of the city skyline.

Fairmont Chicago at Millennium Park

4.5 star property
8.6 out of 10, Excellent, (1827)
"Excellent accommodation, very clean and friendly staff "
The price is CA $334
CA $432 total
includes taxes & fees
Aug 10 - Aug 11
Fairmont Chicago at Millennium Park
Aloft Chicago Mag Mile
Conference room with a large, round table and six chairs, offering city views.

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2780)
"We love our stay here !"
The price is CA $168
CA $198 total
includes taxes & fees
Aug 17 - Aug 18
Aloft Chicago Mag 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.

Top Woodlawn Hotel Reviews

Hilton Chicago

Hilton Chicago

10/10 Excellent
"The main lobby is gorgeous! The view from my room was incredible!"
Beth 2-night trip
Posted 20 hours ago
Hilton Chicago

Frequently asked questions

Searching for romantic hotels in Woodlawn?
If you and your partner need a romantic vacation, we've got just the ticket. If you'd like to explore some of the area's notable sights, you might make a stop by Lake Michigan, 63rd Street Beach, or Lorado Taft's Midway Studios. If you'd like to stay close to a certain attraction, you can sort properties by neighborhood or distance to top landmarks, so you'll be able to see everything on your list.
When is the best time to visit Woodlawn?
The hottest months are usually July and August with an average temperature of 70°F,
  • Coldest months: January, February, December, and March
  • Driest months: November, January, February, and December
  • Rainiest months: June, May, April, and October
What is there to do in Woodlawn?
There's nothing better than experiencing a new place with your sweetheart, so consider checking out all that Woodlawn has to offer. A visit to Lake Michigan, 63rd Street Beach, or Lorado Taft's Midway Studios might be just the ticket when you're checking out the sights.
What's the best way to get to Woodlawn and around town during my romantic getaway?
These transportation options in Woodlawn might help your romantic getaway go off without a hitch: If you're looking to fly in, the closest major airport is Chicago Midway Airport (MDW), located 7.6 mi (12.3 km) away. Make your way to Cottage Grove Station to catch metro.