Beginning of main content

Search over 1,000,000 properties worldwide and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any hotel reservation.


Check Prices on Hotels in The Loop

Tonight 21 Jul. - 22 Jul.
This weekend 26 Jul. - 28 Jul.
Next weekend 2 Aug. - 4 Aug.

Featured The Loop Romantic Hotels

See all 361 properties in The Loop

Estimated price for 1 night/2 adults

LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by Hilton
4.5 out of 5.0 85 East Wacker Drive, Chicago, IL
4.6/5 (2016 reviews)
C$141/ night for 2 guests

Gorgeous space and view. Classic building. Excellent service by all. Super walkable location. My *only* complaint has absolutely nothing to do with the hotel, but the bagpiper who stood on the corner across the street... and played for 8 hours straight every late afternoon into evening. You’ll probably ...

Reviewed on 20 Jul. 2019
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4.0 out of 5.0 17 E Monroe St, Chicago, IL
4.2/5 (12282 reviews)
C$182/ night for 2 guests

A true historic hotel that really speaks to Chicago back in the day. Room was nicely sized, cute bathroom. Easy to walk to all the sights. Great stay!

Reviewed on 20 Jul. 2019
Virgin Hotels Chicago
Virgin Hotels Chicago
4.5 out of 5.0 203 N Wabash Ave, Chicago, IL
Free Cancellation
4.7/5 (2399 reviews)
C$234/ night for 2 guests

we absolutely loved our room! The staff was excellent, comfortable bed, terrific rain shower, 24 room service, very quiet. High tech.... very nice.

Reviewed on 17 Jul. 2019
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5.0 323 E Wacker Dr, Chicago, IL
Free Cancellation
4.4/5 (4154 reviews)
C$187/ night for 2 guests

Self-parking was not well marked AND extremely tight and narrow. Luckily did not scratch the side of my career side mirrors! Also, $57.00 for self parking seems excessive!!!

Reviewed on 20 Jul. 2019
Kimpton Hotel Monaco Chicago
Kimpton Hotel Monaco Chicago
4.5 out of 5.0 225 N Wabash Ave, Chicago, IL
Free Cancellation
4.6/5 (2014 reviews)
C$177/ night for 2 guests

The Kimpton Hotel Monaco was wonderful. My son and I had a great stay. I used valet upon arrival and the valet and bellboy were so kind and helpful. Everyone we came in contact with at the hotel was so nice. When we went out for the day we had uber/lyft and the valet went out of his way to get our ...

Reviewed on 20 Jul. 2019
Wyndham Grand Chicago Riverfront
Wyndham Grand Chicago Riverfront
4.0 out of 5.0 71 E Wacker Dr, Chicago, IL
Free Cancellation
4.4/5 (7756 reviews)
C$176/ night for 2 guests

Building, feel like very expensive hotel 50 years ago.

Reviewed on 18 Jul. 2019
Radisson Blu Aqua Hotel Chicago
Radisson Blu Aqua Hotel Chicago
4.5 out of 5.0 221 N Columbus Dr, Chicago, IL
4.5/5 (1951 reviews)
C$281/ night for 2 guests

Only one elevator. So many peoples were waiting. Take forever to go to my room.

Reviewed on 15 Jul. 2019
theWit Chicago - a DoubleTree by Hilton Hotel
theWit Chicago - a DoubleTree by Hilton Hotel
4.5 out of 5.0 201 N State Street, Chicago, IL
4.5/5 (1765 reviews)
C$227/ night for 2 guests

Tricky review because we had 2 rooms. One room had no issues but my friends in the 2nd room had a clogged sink. The plumber was there until 2am and it still wasn't fixed. Then the hotel called them at 8am to ask them if they could fix it. My friends had to change rooms and ask for compensation. This ...

Reviewed on 17 Jul. 2019
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium Park
4.5 out of 5.0 200 North Columbus Drive, Chicago, IL
Free Cancellation
4.3/5 (2237 reviews)
C$250/ night for 2 guests

Our room layout was very unique. Room amenities were helpful. I wasn't too excited about the food options or service at the hotel restaurant, but overall the restaurant was fine.

Reviewed on 16 Jul. 2019
Map

Romantic Hotels: Our travellers loved these

Estimated price for 1 night/2 adults

Recently Booked Romantic Hotels in The Loop

theWit Chicago - a DoubleTree by Hilton Hotel
4.5 out of 5.0
Last booking: 32 minutes ago
La Quinta Inn & Suites by Wyndham Chicago Downtown
3.0 out of 5.0
Last booking: 59 minutes ago
Hampton Inn Majestic Chicago Theatre District
3.0 out of 5.0
Last booking: 1 hour ago
Kimpton Hotel Allegro
4.0 out of 5.0
Last booking: 1 hour ago
Crowne Plaza Chicago West Loop
3.5 out of 5.0
Last booking: 2 hours ago
Silversmith Hotel Chicago Downtown
4.0 out of 5.0
Last booking: 2 hours ago
Residence Inn Chicago Downtown/Loop
3.5 out of 5.0
Last booking: 2 hours ago
Hilton Chicago- Michigan Ave Cultural Mile
4.0 out of 5.0
Last booking: 2 hours ago
Palmer House a Hilton Hotel
4.0 out of 5.0
Last booking: 3 hours ago

Romantic Hotels and Accommodations in The Loop


Are you looking for a romantic getaway? Whether you want to lounge around in luxurious bedding or share a candlelit dinner, you can find ways to spend quality time with your partner in The Loop. Our guests also love The Loop for its stunning architecture, top museums, and popular art scene. If you want to explore the area, you might head to Millennium Park, Willis Tower, or Skydeck Ledge. If you're looking for specific amenities to make your romantic getaway even more magical, we can help you plan for that. When you search for a place to stay on Expedia.com, it's easy to filter properties by amenity and find an accommodation that's a perfect fit. If you're interested in staying near a certain attraction, you can sort properties by neighborhood and proximity to top sights, so you'll be able to see everything on your list.


When is the Best Time to Visit The Loop?


Weather can be an important factor for your holiday, so we've provided rainfall and temperature stats 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 The Loop


There's nothing better than seeing a new destination with your sweetheart, so consider taking time to discover all there is to see and do in The Loop. If you're hoping to experience some of the local culture, you'll love The Loop for its stunning architecture, top museums, and popular art scene. You might think about stopping by Millennium Park, Willis Tower, or Skydeck Ledge while you're seeing the sights.


Travelers also enjoy The Loop for its:
  • Skyscrapers
  • Entertainment
  • Shopping
  • Restaurants
  • Monuments

Getting Around The Loop


To get to The Loop, book a flight to Chicago, IL (MDW-Midway Intl.), which is the closest major airport, located 8.6 mi (13.9 km) from the city center. Walk to nearby metro stations like Adams-Wabash Station, Jackson Station, and Harold Washington Library Station. If you want to journey outside of the area, ride aboard a train from Chicago Van Buren Street Station, Millennium Station, or Chicago Museum Campus-11th Street Station.