Find Romantic Hotels in Downtown Chicago from S$216

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check availability on Downtown Chicago Romantic Hotels

Top Romantic Hotels in Downtown Chicago

LondonHouse Chicago, Curio Collection by Hilton
Contemporary lounge area with a striking metal structure and large windows offering urban views.

LondonHouse Chicago, Curio Collection by Hilton

4.5 star property
9.4 out of 10, Exceptional, (3347)
"Great stay"
The price is S$256
includes taxes & fees
10 Aug - 11 Aug
LondonHouse Chicago, Curio Collection by Hilton
Palmer House a Hilton Hotel
Experience the grandeur of our elegantly decorated lobby, featuring a stunning chandelier, comfortable seating areas, and intricate designs.

Palmer House a Hilton Hotel

4.0 star property
8.4 out of 10, Very good, (1787)
"Love this hotel"
The price is S$304
includes taxes & fees
6 Aug - 7 Aug
Palmer House a Hilton Hotel
Trump International Hotel & Tower Chicago
Enjoy breathtaking views of the city skyline from the expansive window.

Trump International Hotel & Tower Chicago

5.0 star property
9.4 out of 10, Exceptional, (1639)
"Great hotel "
The price is S$705
includes taxes & fees
20 Jul - 21 Jul
Trump International Hotel & Tower Chicago
The Peninsula Chicago
Stylish hotel building with a unique architectural design, set amidst a vibrant urban landscape.

The Peninsula Chicago

5.0 star property
9.8 out of 10, Exceptional, (1004)
"Excellent very clean Quiet great location"
The price is S$939
includes taxes & fees
20 Jul - 21 Jul
The Peninsula Chicago
Eurostars Magnificent Mile
Enjoy a meal with a view at this restaurant, offering a variety of seating options and a central bar area.

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (3037)
"Loved our stay! "
The price is S$216
includes taxes & fees
24 Jul - 25 Jul
Eurostars Magnificent Mile
Virgin Hotels Chicago
Relax on the rooftop with a mix of seating options and potted plants, overlooking a historic building and modern skyscrapers.

Virgin Hotels Chicago

4.5 star property
9.2 out of 10, Wonderful, (1340)
"Very well appointed rooms and wonderful customer service!!"
The price is S$428
includes taxes & fees
27 Jul - 28 Jul
Virgin Hotels Chicago
Sofitel Chicago Magnificent Mile
Stunning city views from the sleek, contemporary hotel building.

Sofitel Chicago Magnificent Mile

4.5 star property
9.4 out of 10, Exceptional, (2072)
"Great stay!!!"
The price is S$374
includes taxes & fees
10 Aug - 11 Aug
Sofitel Chicago Magnificent Mile
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, (2418)
"Amazing Stay!"
The price is S$325
includes taxes & fees
7 Aug - 8 Aug
Swissotel - Chicago
Hampton Inn Chicago Downtown/Magnificent Mile
Enjoy a panoramic city view from the comfort of your room, featuring a large window and a neatly made bed with a headboard that extends to the window.

Hampton Inn Chicago Downtown/Magnificent Mile

2.5 star property
8.2 out of 10, Very good, (1345)
"Good place to stay downtown"
The price is S$239
includes taxes & fees
6 Aug - 7 Aug
Hampton Inn Chicago Downtown/Magnificent Mile
L7 Chicago by LOTTE
Stunning hotel exterior with a sleek glass canopy and modern design.

L7 Chicago by LOTTE

4.5 star property
9.6 out of 10, Exceptional, (2646)
"Very nice location and great restaurant on the premises "
The price is S$346
includes taxes & fees
10 Aug - 11 Aug
L7 Chicago by LOTTE
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 Michigan Avenue, Navy Pier or Lake Michigan. 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 Michigan Avenue, Navy Pier or Lake Michigan.
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.