The Loop Vacations from $618
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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.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $957, price is now $618 per person
$618
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,070 reviews)
Very clean and spacious! Friendly staff Generous breakfast tho coffee could be much better ditto tea…both like dishwater if British take t-bags! If coffee fan have elsewhere.
And no water in rooms after first night. Apart from those niggles beds very comfy enjoyable stay…roof top bar a must!
Reviewed on May 12, 2026
The Wade
Downtown Chicago
Save 100% on your flight
Price was $1,754, price is now $1,032 per person
$1,032
per person
Jun 17 - Jun 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,825 reviews)
Lovely hotel, very modern and clean. Had fantastic views from the top floor. We were on floor 28 and the skyline was great. Bed very comfortable and it was expected from a 4* hotel. Chicago is a business city, reminded me of a bar man set as its high rised buildings and slightly darker from the shadows of these buildings. Locally there was a few cafes and coffee shops for easy reach for breakfast
Reviewed on May 11, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $963, price is now $624 per person
$624
per person
Jun 22 - Jun 25
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (472 reviews)
Love the amenities. Great location too
Reviewed on May 3, 2026
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
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
$135 nightly
The price is $161 total per night from May 25 to May 26
$161 total
May 25 - May 26
Total with taxes and fees
8/10 Very Good! (10,220 reviews)
The bar being open late is nice and the staff are very helpful.
Reviewed on May 12, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $167 total per night from May 25 to May 26
$167 total
May 25 - May 26
Total with taxes and fees
8.8/10 Excellent! (5,162 reviews)
Friendly staff and excellent location. Loved our 2 bed suite with 2 bathrooms and a kitchen! Would absolutely stay again!
Reviewed on May 11, 2026
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street Chicago IL
$144 nightly
The price is $172 total per night from May 25 to May 26
$172 total
May 25 - May 26
Total with taxes and fees
8.8/10 Excellent! (3,521 reviews)
Definitely In going to this hotel again soon Very nice hotel staff and clean and the location was great
Reviewed on May 12, 2026
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
4.5/5(7,309 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Chicago Riverwalk
4.5/5(1,558 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.
Willis Tower
4.5/5(3,420 reviews)
Visit the Skydeck and gaze down over the Chicago cityscape from a dazzling 1,353 feet above the sidewalk.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
96% of travellers recommend
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- Chicago Vacations
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- 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.