The Loop Vacations from $242
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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 Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $401, price is now $242 per person
$242
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.
Reviewed on Nov 26, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $699, price is now $434 per person
$434
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
It's always perfection at the Trump. King suite with Lake view is the ultimate
Reviewed on Dec 2, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $424, price is now $265 per person
$265
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean room. Attentive staff. Amazing breakfast buffet. Great location.
Reviewed on Dec 7, 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Save 100% on your flight
Price was $715, price is now $450 per person
$450
per person
Jan 27 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
The Chicago Athletic Association Hotel is the most charming hotel in the city of Chicago. My wife and I recently got married in Chicago and one of the highlights of the weekend was hanging out at the hotel! It has a roaring 20's vibe with the dark woods in the main lobby and the large game room which is a fun place to get a drink and play chess/pool. Amazing location close to the Amtrak, Chicago subway, and the South shore railroad. And it's across the street from Millennium Park. Most importantly, the staff is very professional and attentive and will go above and beyond to make your stay perfect. I always stay at this hotel when I go to Chicago because of it's charm and service. I would never stay anywhere else because it's a truly unique hotel in an awesome location with the nicest and most professional staff. 10/10 recommend to anyone!
Reviewed on Nov 20, 2025
La Banque Hotel
Save 100% on your flight
Price was $640, price is now $404 per person
$404
per person
Feb 20 - Feb 23
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
The room was spotless and the staff was good. Loved the hotel. Was just an overnight stay. Wish we had stayed another day. Loved the area.
Reviewed on Nov 30, 2025
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
Downtown Chicago
5 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.
The Loop Hotel Deals
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $145 total per night from Dec 28 to Dec 29
$145 total
Dec 28 - Dec 29
Total with taxes and fees
8.4/10 Very Good! (2,115 reviews)
great stay
Reviewed on Dec 5, 2025
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $116 total per night from Dec 11 to Dec 12
$116 total
Dec 11 - Dec 12
Total with taxes and fees
8.6/10 Excellent! (1,965 reviews)
Clean room. Convenient
Reviewed on Dec 4, 2025
Silversmith Hotel Chicago Downtown
10 S Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $149 total per night from Jan 4 to Jan 5
$149 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.2/10 Wonderful! (2,102 reviews)
Close to some great restaurants and shopping.
Reviewed on Dec 6, 2025
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.
Discover the most popular places to visit in The Loop
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Chicago Riverwalk
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.
Willis Tower
Visit the Skydeck and gaze down over the Chicago cityscape from a dazzling 1,353 feet above the sidewalk.
Things to do
Chicago Bulls Basketball Game at United Center
$98
per adult
80% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$45
per adult
94% of travellers recommend
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- Chicago Vacations
- Visit Downtown Chicago
- Visit Chicago
- Where to stay in Chicago
- Daley Plaza
- Chicago Theatre
- Picasso Statue
- Chase Tower
- Willis Tower
- Marshall Field Building
- Richard J. Daley Center
- Noble Fool Theater
- Goodman Theater
- Miró's Chicago
- Chicago Riverwalk
- Chicago Temple
- State Street
- Chicago Cultural Center
- Sullivan Center
- Chicago City Hall
- Navy Pier
- Millennium Park
- Chicago Loop Synagogue
- Chagall's Four Seasons
- CIBC Theatre
- Cadillac Palace Theatre
- Art Institute of Chicago
- Haskell Building
- Cloud Gate
- Marina City
- Carbide and Carbon Building
- Marquette Building
- House of Blues Chicago
- Aon Center
- Crown Fountain
- Rookery
- Chicago Board of Trade Building
- Harris Theater
- Harold Washington Library Center
- Museum of Broadcast Communications
- Monadnock Building
- DePaul University-Loop Campus
- 333 West Wacker Drive
- Symphony Center
- Chicago Symphony Orchestra
- Skydeck Ledge
- Michigan Avenue Bridge
- Civic Opera House
- Fisher Building
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.