Find Romantic Hotels in Downtown Chicago from S$216

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Top Romantic Hotels in Downtown Chicago

The Peninsula Chicago
Front of property – evening/night
The Peninsula Chicago
5.0 star property
9.8 out of 10, Exceptional, (1005)
"We had an outstanding experience and stay! They reached out prior to our arrival and asked if they could pre-arrange anything and what time we were arriving. We said we’re celebrating our anniversary and will arrive at noon. Upon check-in at noon, our room was ready and they upgraded us! When we returned to our room later that day we were greeted with champagne and chocolate covered strawberries. A very thoughtful and unexpected surprise we greatly appreciated. Accommodations, pool and spa are...
The price is S$833
per night
23 May - 24 May
The Peninsula Chicago
L7 Chicago by LOTTE
Exterior
L7 Chicago by LOTTE
4.5 star property
9.4 out of 10, Exceptional, (1003)
"The rooms were very spacious and clean. It was a short walk to Millennium park as well as Magnificent mile. The lobby and restaurant were under construction but looked like a great space once done. "
The price is S$332
per night
27 May - 28 May
L7 Chicago by LOTTE
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Property amenity
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
4.5 star property
9.4 out of 10, Exceptional, (1000)
"Excellent location! Luigi was very personable and helpful throughout our stay."
The price is S$445
per night
11 May - 12 May
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
LondonHouse Chicago, Curio Collection by Hilton
Lobby
LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
9.2 out of 10, Wonderful, (3505)
"Location, location, location!!"
The price is S$323
per night
27 May - 28 May
LondonHouse Chicago, Curio Collection by Hilton
Trump International Hotel & Tower Chicago
Terrace/patio
Trump International Hotel & Tower Chicago
5.0 star property
9.2 out of 10, Wonderful, (1186)
"It was great! Perfect service, room was clean and beautiful! There was a hole in the wall though and a few dents near the chair. But it was still great and we loved it! We will definitely be back! "
The price is S$589
per night
23 May - 24 May
Trump International Hotel & Tower Chicago
Virgin Hotels Chicago
Rooftop terrace
Virgin Hotels Chicago
4.5 star property
9.2 out of 10, Wonderful, (1007)
"This hotel is top notch! The most comfortable bed, linens and pillows ever….they have thought of everything, including little things like the time is displayed in red light letters on the ceiling during the night, near the bed! We enjoyed the restaurant for breakfast and the rooftop bar was so fun for drinks and small plates…the views were wonderful! Our room was spotless and every staff person we came across was friendly, professional and very helpful! We had a fabulous two night stay and would...
The price is S$413
per night
27 May - 28 May
Virgin Hotels Chicago
Sofitel Chicago Magnificent Mile
Exterior
Sofitel Chicago Magnificent Mile
4.5 star property
9.2 out of 10, Wonderful, (1367)
"Sofitel is our favorite Chicago hotel. Great service, amazing rooms and perfectly placed among our favorite shops and restaurants. The food at Le Bar and the restaurant are excellent. Also, they have the MLB channel, so if you're in town for a Cubs game, you can start your morning with baseball and wind down your night with baseball."
The price is S$339
per night
12 May - 13 May
Sofitel Chicago Magnificent Mile
The Royal Sonesta Chicago Downtown
Exterior
The Royal Sonesta Chicago Downtown
4.0 star property
9.0 out of 10, Wonderful, (1925)
"All around great location and stay"
The price is S$371
per night
27 May - 28 May
The Royal Sonesta Chicago Downtown
Ambassador Chicago, part of JdV by Hyatt
Terrace/patio
Ambassador Chicago, part of JdV by Hyatt
4.0 star property
8.8 out of 10, Excellent, (1003)
"Cool old hotel in a great location. "
The price is S$291
per night
27 May - 28 May
Ambassador Chicago, part of JdV by Hyatt
Swissotel - Chicago
Front of property – evening/night
Swissotel - Chicago
4.5 star property
8.6 out of 10, Excellent, (1971)
"It’s located in a very convenient and quiet area of downtown."
The price is S$347
per night
11 May - 12 May
Swissotel - Chicago
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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.

Frequently asked questions

Searching for romantic hotels in Downtown Chicago?
Are you and your partner looking for a romantic holiday? Our guests also love Downtown Chicago for its stunning architecture, top museums and popular theatre scene. You might consider checking out some of the nearby sights and attractions such as Grant Park, Navy Pier or Millennium Park. If you’re interested in staying close to a certain attraction, you can sort by neighbourhood and proximity to top sights, so you’ll be able to see everything on your list.
What's the best accommodation for a romantic holiday in Downtown Chicago?
Congress Plaza Hotel is a favourite hotel for couples, and features deep-soaking baths and cable TV. Other good options for a romantic stay include Eurostars Magnificent Mile and InterContinental Chicago Magnificent Mile, an IHG Hotel.
How many romantic hotels can we expect to find in Downtown Chicago?
Expedia has 18 romantic Downtown Chicago hotels for you to get cosy in.
#### When is the Best Time to Visit Downtown Chicago?\n
  • Hottest months: July, August, June and September, with an average temperature of 21°C
  • 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 Downtown Chicago?
There’s nothing better than wandering around a new destination with your sweetheart, so consider checking out all there is to see and do in Downtown Chicago. If you’re hoping to experience some of the local culture, you’ll love Downtown Chicago for its stunning architecture, top museums and popular theatre scene. You might think about visiting Grant Park, Navy Pier or Millennium Park.
What's the best way to get to Downtown Chicago and around town during my romantic getaway?
This information about transportation options in Downtown Chicago might help your romantic trip get off to a smooth start: If you’re looking to fly in, the closest major airport is iChicago Midway Airport (MDW), located 8.9 mi (14.3 km) away. Nearby metro stations include State Station, Clark-Lake Station and Lake Station.