Romantic in Chicago

Browse for Chicago Romantic Hotels from $99

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Featured Chicago Romantic Hotels

Image for The Champagne Lodge & Luxury Suites
3.5 out of 5
16 W 621 S. Frontage Rd, Willowbrook, IL
$99
per night
Sep 23 - Sep 24
4.3/5Excellent! (1,505 reviews)

"Clean room, nice fireplace, loved the jacuzzi, overall a great place"…"

Reviewed on Sep 15, 2019

The Champagne Lodge & Luxury Suites
Image for LondonHouse Chicago, Curio Collection by Hilton
4.5 out of 5
85 East Wacker Drive, Chicago, IL
Free CancellationPay later
$153
per night
Sep 29 - Sep 30
4.6/5Exceptional! (2,189 reviews)

"Great location, spacious room, comfy beds Location location location!!!"…"

Reviewed on Sep 18, 2019

LondonHouse Chicago, Curio Collection by Hilton
Image for Palmer House a Hilton Hotel
4 out of 5
17 E Monroe St, Chicago, IL
Free CancellationPay later
$176
per night
Sep 27 - Sep 28
4.2/5Excellent! (12,544 reviews)

"great location, great staff and amenities, beautiful property"…"

Reviewed on Sep 17, 2019

Palmer House a Hilton Hotel
Image for Trump International Hotel & Tower Chicago
5 out of 5
401 N Wabash Ave, Chicago, IL
Free CancellationPay later
$276
per night
Oct 6 - Oct 7
4.8/5Exceptional! (2,022 reviews)

"We have stayed in a lot of beautiful hotels and now count this as one of our favorites. The location and views were excellent and the staff ans service were impeccable. We had forgotten to bring deodorant and asked if the hotel could send up a little speed stick, by the time we came back from coffee, ..."…"

Reviewed on Sep 16, 2019

Trump International Hotel & Tower Chicago
Image for The Peninsula Chicago
5 out of 5
108 East Superior Street, Chicago, IL
Free CancellationPay later
$399
per night
Sep 29 - Sep 30
4.9/5Exceptional! (1,250 reviews)

"Great services, amazing rooms, delicious breakfast, best hotel in Chicago."…"

Reviewed on Sep 15, 2019

The Peninsula Chicago
Image for Eurostars Magnificent Mile, previously Dana Hotel
4 out of 5
660 North State Street, Chicago, IL
Free Cancellation
$134
per night
Sep 30 - Oct 1
4.4/5Wonderful! (2,160 reviews)

"Very centrally located, a wallway to all the things to do in Chicago. The staff was friendly, the concierge mde things jappen for us.. i highlt recommend the gotel for a bisit to downtown Chicago."…"

Reviewed on Sep 16, 2019

Eurostars Magnificent Mile, previously Dana Hotel
Image for The Herrington Inn & Spa
4 out of 5
15 S River Ln, Geneva, IL
Free CancellationPay later
$189
per night
Sep 22 - Sep 23
4.7/5Exceptional! (154 reviews)

"Loved this quaint, historic hotel. Took my high school godchildren here, and the teens loved it. Awesome amenities including turn down service (milk and cookies especially, true to their history), great breakfast, and probably the nicest hotel bathroom I've ever been in. We stayed on the first floor ..."…"

Reviewed on Aug 19, 2019

The Herrington Inn & Spa
Image for Virgin Hotels Chicago
4.5 out of 5
203 N Wabash Ave, Chicago, IL
Free CancellationPay later
$179
per night
Oct 6 - Oct 7
4.7/5Exceptional! (2,448 reviews)

"Loved the location. Easy walking distance to pretty much everything downtown. Staff is efficient, helpful & very courteous. They truly seemed as if they were enjoying their jobs! Room was very clean, plenty of space. Rooftop bar is a must, amazing view."…"

Reviewed on Sep 16, 2019

Virgin Hotels Chicago
Image for Sofitel Chicago Magnificent Mile
4.5 out of 5
20 E Chestnut St, Chicago, IL
Free CancellationPay later
$183
per night
Sep 27 - Sep 28
4.6/5Exceptional! (2,209 reviews)

"Great location, love the bar, lovely room! Friendly and accommodating staff."…"

Reviewed on Sep 16, 2019

Sofitel Chicago Magnificent Mile
Image for Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Free CancellationPay later
$159
per night
Sep 29 - Sep 30
4.4/5Excellent! (4,188 reviews)

"The view from this hotel was perfect. Truly allows you to enjoy the Chicago skyline."…"

Reviewed on Sep 16, 2019

Swissotel - Chicago
Image for Hampton Inn Chicago Downtown/Magnificent Mile
2.5 out of 5
160 E Huron Street, Chicago, IL
Free CancellationPay later
$225
per night
Sep 29 - Sep 30
4.2/5Excellent! (3,744 reviews)

"Our room was “Magnificent”, spacious and very clean. The only change we would make is to the mattress of the sofa bed, one can feel the springs in ones back"…"

Reviewed on Sep 16, 2019

Hampton Inn Chicago Downtown/Magnificent Mile
Image for Kimpton Hotel Monaco Chicago
4.5 out of 5
225 N Wabash Ave, Chicago, IL
Free CancellationPay later
$159
per night
Sep 30 - Oct 1
4.6/5Exceptional! (2,034 reviews)

"The decor is very unique, everything is super clean, and the bathrooms are so high end."…"

Reviewed on Sep 3, 2019

Kimpton Hotel Monaco Chicago
Image for Raffaello Hotel
4 out of 5
201 E Delaware Pl, Chicago, IL
$139
per night
Sep 22 - Sep 23
4.1/5Very Good! (2,326 reviews)

"What I liked about the property is the location in the downtown close to so many attractions Also I liked that the size of the room was big What I didn’t like is that we requested a crib for my 11 months old baby and it was very unclean and broken The staff are not very friendly and the receptionist ..."…"

Reviewed on Aug 27, 2019

Raffaello Hotel
Image for Wyndham Grand Chicago Riverfront
4 out of 5
71 E Wacker Dr, Chicago, IL
Free CancellationPay later
$159
per night
Sep 29 - Sep 30
4.4/5Excellent! (7,957 reviews)

"Very clean and great service staff. Long wait at times for elevators, but is to be expected in a busy hotel. Noisy neighbors, but that too is expected when they host weddings and parties in the penthouse."…"

Reviewed on Sep 13, 2019

Wyndham Grand Chicago Riverfront
Image for Radisson Blu Aqua Hotel Chicago
4.5 out of 5
221 N Columbus Dr, Chicago, IL
Free CancellationPay later
$198
per night
Oct 6 - Oct 7
4.5/5Wonderful! (1,982 reviews)

"I liked having a balcony as part of room with great views of the city. The bathroom was beautiful but floor could become slippery when wet. The pool was not pristine and the pool room itself needs a better ventilation system. Service was excellent and employees were very helpful. I would recommend ..."…"

Reviewed on Sep 16, 2019

Radisson Blu Aqua Hotel Chicago
Image for The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
4.5 out of 5
521 North Rush Street, Chicago, IL
Free CancellationPay later
$179
per night
Sep 29 - Sep 30
4.6/5Wonderful! (1,957 reviews)

"Perfect location in downtown Chicago! We had a great time, hotel was quiet, bed and pillows comfortable!"…"

Reviewed on Aug 24, 2019

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Image for Ambassador Chicago
4 out of 5
1301 N State Pkwy, Chicago, IL
Free CancellationPay later
$166
per night
Sep 30 - Oct 1
4.2/5Excellent! (2,060 reviews)

"Friendly, very helpful staff, excellent location, Very clean"…"

Reviewed on Sep 17, 2019

Ambassador Chicago
Image for Waldorf Astoria Chicago
5 out of 5
11 E. Walton Street, Chicago, IL
Free CancellationPay later
$281
per night
Sep 30 - Oct 1
4.7/5Exceptional! (958 reviews)

"First of all, when you walk in, it’s the most Pleasant smell ever ! Check in its super fast and easy, very friendly staff. I will never stay anywhere else. It’s so luxurious! The rooms have these amazing size soaking tubs, and luxury products."…"

Reviewed on Sep 10, 2019

Waldorf Astoria Chicago
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Romantic Hotels and Accommodations in Chicago

If you and your partner need a romantic escape, we'd like to help you plan for it. Couples choose Chicago for its popular theater scene and scenic landscape. If you're a pair that loves cultural attractions, you might check out Chicago Cultural Center, Ford Center for the Performing Arts Oriental Theatre, or Chicago Theatre.

If you and your sweetheart are looking forward to a relaxing time away or you're hoping to staying near top romantic sights, you can take your pick of 289 lodging options in Chicago for the ideal romantic vacation.

Expedia travelers pick these hotels and lodging options for their romantic atmosphere and amenities:

Swissotel - Chicago: This 4.5-star hotel offers spa treatment rooms, a restaurant, and 2 bars. Our guests appreciate its spacious rooms and proximity to public transportation.

Raffaello Hotel: 4-star hotel featuring a restaurant, a bar, and free WiFi. Customers give positive reviews for its comfortable rooms.

Palmer House a Hilton Hotel: With a stay at this 4-star hotel, you'll have access to couples' treatment rooms, a spa tub, and an indoor pool. Expedia travelers speak highly of its proximity to shopping.

Trump International Hotel & Tower Chicago: 5-star hotel featuring massages, an indoor pool, and a restaurant. Customers give positive reviews for its comfortable rooms.

When is the Best Time to Visit Chicago?

Weather can be a major factor for your romantic getaway, so we've collected rainfall and seasonal temperature info to help you pick the best travel dates:

  • Hottest months: July, June, August, and September, with an average temperature of 83°F
  • Coldest months: January, February, December, and March, with an average temperature of 20°F
  • Driest months: February, January, December, and March, with an average rainfall of 2.31 inches
  • Rainiest months: May, June, July, and August, with an average rainfall of 4.05 inches

Sightseeing in and Around Chicago

There's nothing better than experiencing a new place 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 theater scene, stunning architecture, and top museums. You might consider a visit to Millennium Park, Willis Tower, or Skydeck Ledge.

Travelers also enjoy Chicago for its:
  • Skyscrapers
  • Monuments
  • Entertainment
  • Shopping

Getting Around Chicago

If you're looking to fly to Chicago, the closest major airport is in Chicago, IL (MDW-Midway Intl.), located 8.6 mi (13.9 km) from the city center. Nearby metro stations include Monroe Station, Monroe Station, and Adams-Wabash Station. If you want to see more of the area, hop aboard a train from Millennium Station, Chicago Van Buren Street Station, or Chicago Union Station.

More trip options

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