The Loop Vacations from $498

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Your The Loop Vacation

Experience the best that The Loop has to offer with a tailor-made The Loop vacation package. From its bars and pubs and history to its festivals, get ready to fall for the charms of this food-lovers neighborhood. Your trip to The Loop wouldn't be complete without seeing popular attractions nearby such as Millennium Park, Willis Tower and Art Institute of Chicago. Expedia can help you turn your ideal The Loop vacation into reality, no matter your budget or travel plans.

The Latest The Loop Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
Save 100% on your flight
$498
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$774
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
The hotel room is clean but blood stain spotted on the bedsheet.

Reviewed on Sep 23, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
$629
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
I loved the balcony and the great view! The kitchenette was a plus along with the provided utensils and necessary items. The laundry are was not something that I used but I could see how it would be a bonus feature. The area by the bed was a little cramped, but it ended up being comfortable. The staff was extremely friendly and helpful and the check in was seamless. The elevators were especially private and convenient. Overall, the extra $ that I paid for my stay was well worth it!

Reviewed on Sep 21, 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
Save 100% on your flight
$593
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
Save 100% on your flight
$526
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,681 reviews)

Where to stay in The Loop

Find the best The Loop areas and neighborhoods for the activities you enjoy most. Learn more about The Loop
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago
A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

Find hotels in Magnificent Mile
A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

Find hotels in River North
A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

Find hotels in Lincoln Park
A cityscape with modern skyscrapers and a curved highway.

West Loop

Consider a visit to The Old Post Office and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center.

Find hotels in West Loop

The Loop Hotel Deals

River Hotel

River Hotel

75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$171 nightly
$203 total
Oct 25 - Oct 26
Total with taxes and fees
8.8/10 Excellent! (5,435 reviews)
"Elevator was broken, took 15 minutes each time I needed it"

Reviewed on Sep 24, 2026

River Hotel
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$153 nightly
$182 total
Oct 25 - Oct 26
Total with taxes and fees
8/10 Very Good! (10,199 reviews)
"Very loud with nearby trains. Convenient location, beautiful lake view and a lovely old hotel, but needs to be updated with new bedding, a properly sized rug, and outlets for phones/tablets. Parking is $62 in an open parking lot. Staff was not friendly at check-in."

Reviewed on Sep 23, 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$185 nightly
$220 total
Oct 24 - Oct 25
Total with taxes and fees
8.6/10 Excellent! (3,261 reviews)
"Very clean. Great location. Close to shopping, restaurants and the lake. Highly recommend"

Reviewed on Sep 23, 2026

Hilton Chicago
See all 1,163 properties in 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations
Golf Vacations
Golf Vacations
Luxury Vacations
Luxury Vacations
Romantic Vacations
Romantic Vacations
Ski Vacations
Ski Vacations
Gay Friendly Vacations
LGBTQ Friendly Vacations
LGBTQ Friendly Vacations
Adventure Vacations
Adventure Vacations
Vacations in Month
Where to go when
Where to go when
Honeymoon Vacations
Honeymoon Vacations
Mountain Vacations
Mountain Vacations
Fishing Vacations
Fishing Vacations
Adults Only Vacations
Adults Only Vacations
Waterpark Vacations
Waterpark Vacations
Scuba Diving Vacations
Scuba Diving Vacations
Yoga Vacations
Yoga Vacations
Cheap Vacations
Cheap Vacations
Solo Vacations
Solo Vacations

Stay near popular The Loop attractions

A large metallic sphere sculpture in a public square surrounded by tall buildings.
Photo by TM

Millennium Park

9.4/10 (30,446 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
See properties
A cityscape at night with illuminated buildings, a river, and a bridge.
Photo by TM

Chicago Riverwalk

9.6/10 (13,574 reviews)
Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.
See properties
A city skyline with tall skyscrapers, a river, and a bridge.

Willis Tower

9.0/10 (9,893 reviews)
Visit the Skydeck and gaze down over the Chicago cityscape from a dazzling 1,353 feet above the sidewalk.
See properties
The Art Institute of Chicago building with classical architecture, a lion statue, and banners advertising events.

Art Institute of Chicago

9.4/10 (7,898 reviews)
Explore a massive collection of works celebrating different cultures and historical times, from ancient Egypt to modern installations.
See properties
A large illuminated sign with the letters "CHICA" and a circular design.
Photo by © Choose Chicago

Chicago Theatre

9.0/10 (1,866 reviews)
See a stage show at this iconic cultural beacon, which still captures all the splendor of a trip to the movie theater in the early 20th century.
See properties
A cityscape with a prominent modern sculpture in the foreground and a mix of historic and contemporary buildings in the background.

Cloud Gate

9.4/10 (104 reviews)
You can learn about the history of Chicago with a stop at Cloud Gate. Discover the fascinating museums and notable monuments in this vibrant area.
See properties
A grand hall with a high, ornate ceiling and intricate architectural details.
Photo by TM

Chicago Cultural Center

9.2/10 (220 reviews)
Enjoy a stop at Chicago Cultural Center, an entertaining place to visit in Chicago. Discover the fascinating museums and notable monuments in this vibrant area.
See properties

Auditorium Building and Theatre

8.6/10 (56 reviews)
You can make plans for a show at Auditorium Building and Theatre during your trip to Chicago. Discover the acclaimed art scene and notable monuments in this vibrant area.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$24
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Flyover in Chicago

Flyover in Chicago

$38
per adult
98% of travellers recommend
Flyover in Chicago
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Chicago

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.