A river with yellow boats, a bridge, and tall buildings.

Find Romantic Hotels in The Loop, Chicago from CA $196

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Check availability on The Loop Romantic Hotels

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Our top choices for The Loop romantic hotels

1. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,234 reviews)
"The room was clean and the building was nostalgic."
United States
John
The price is CA $258
CA $307 total
includes taxes & fees
Oct 30 - Oct 31
Hilton Vacation Club Hotel Blake Chicago

2. Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (10,137 reviews)
"Room were clean and comfortable and staff was helpful."
United States
Guadalupe
The price is CA $165
CA $196 total
includes taxes & fees
Nov 2 - Nov 3
Congress Plaza Hotel

3. River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (5,462 reviews)
"Great stay! Will definitely recommend to others visiting the city."
United States
Charlie
The price is CA $225
CA $267 total
includes taxes & fees
Nov 2 - Nov 3
River Hotel

4. citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4,374 reviews)
"Great location and friendly staff"
United States
Kimberly
The price is CA $242
CA $287 total
includes taxes & fees
Nov 1 - Nov 2
citizenM Chicago Downtown

5. LIVN - Millennium Park Downtown Chicago

LIVN - Millennium Park Downtown Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (209 reviews)
"Amazing stay! Not one issue, the virtual check in and parking was easy. Would stay again!"
United States
Rebecca
The price is CA $407
CA $478 total
includes taxes & fees
Oct 4 - Oct 5
LIVN - Millennium Park Downtown Chicago

6. The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2,924 reviews)
"Very helpful staff and excellent location."
United States
David
The price is CA $182
CA $262 total
includes taxes & fees
Nov 1 - Nov 2
The Allegro Royal Sonesta Hotel Chicago Loop

7. Arlo Chicago

Arlo Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,385 reviews)
"Arlo is such a chic hotel!"
United States
Ashley Nacole
The price is CA $232
CA $320 total
includes taxes & fees
Nov 1 - Nov 2
Arlo Chicago

8. The Wade

The Wade
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,110 reviews)
"Had a wonderful stay here"
United States
Erin
The price is CA $181
CA $215 total
includes taxes & fees
Nov 1 - Nov 2
The Wade

9. Hampton Inn Majestic Chicago Theatre District

Hampton Inn Majestic Chicago Theatre District
3.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,001 reviews)
"we liked our stay here"
United States
Michael
The price is CA $209
CA $248 total
includes taxes & fees
Nov 2 - Nov 3
Hampton Inn Majestic Chicago Theatre District

10. Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,184 reviews)
"Very comfortable beds and friendly, helpful staff."
United States
Myra
The price is CA $238
CA $325 total
includes taxes & fees
Nov 1 - Nov 2
Staypineapple, An Iconic Hotel, The Loop
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.

Find out more about The Loop

The Loop attractions for couples

The Loop, the vibrant heart of Chicago, offers a wealth of experiences that cater to the discerning traveller. Begin your adventure at Millennium Park, where you can marvel at the iconic Cloud Gate sculpture, affectionately known as "The Bean," and enjoy the lush gardens surrounding it. Just a short stroll away is the Art Institute of Chicago, home to an extensive collection of Impressionist masterpieces and contemporary works, perfect for art enthusiasts. For a taste of Chicago’s history, visit the Chicago Cultural Center, renowned for its stunning Tiffany stained-glass dome and free cultural events. Families will delight in the interactive exhibits at the Field Museum, where you can encounter ancient fossils and explore the wonders of our planet. After a day of exploration, unwind in one of The Loop’s luxurious hotels, such as the JW Marriott Chicago, where you can indulge in a lavish spa treatment or enjoy a fine dining experience with views overlooking the city. The Loop’s central location means you can easily access top attractions while enjoying the convenience of high-top hotels, making it a perfect base for adventurous families seeking both comfort and culture.

Top The Loop Hotel Reviews

Frequently asked questions

Searching for romantic hotels in The Loop?
If you and your partner need some romantic time away, we've got just the ticket. Couples choose The Loop for its popular theater scene and top-notch restaurants. If you want to spend some time strolling through captivating scenery with your love, you might make a visit to Millennium Park, Grant Park, or Maggie Daley Park. Whether you'd like to be pampered with breakfast in bed or have a romantic dinner by candlelight, you'll be sure to find accommodation in The Loop to make for the perfect couples' weekend.
What's the best hotel for a couple visiting The Loop?
Downtown Printer Row district Hotel style room is a favorite hotel for couples, and features jetted bathtubs and a fitness center.
What is there to do in The Loop?
There's nothing better than seeing a new destination with your sweetheart, so consider checking out 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 Michigan Avenue, Lake Michigan, or Daley Plaza while you're seeing the sights.
What's the best way to get to The Loop and around town during my romantic getaway?
These transportation options in The Loop might help your romantic getaway go off without a hitch: The closest major airport is Chicago Midway Airport (MDW), located 8.8 mi (14.1 km) away. Nearby metro stations include Washington Station, Lake Station, and State Station.

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