The Loop Vacations
Book a Hotel + Flight or Car together to unlock savings
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.
Price found within the past 48 hours. Click for updated prices.
- La Banque Hotel
Jul 18 - Jul 21La Banque Hotel + Flight
Homewood3 nights9.4/10 - Exceptional (494 reviews)"Great team of staff. I requested to check in early and front desk staff were so sweet and allowed me to have my room 3 hours before 3pm. Amazing hotel. Nice breakfast. It was not fancy but the quality was exellent. Super close to the Met train station. All and all. I was very pleased."Reviewed May 16, 2026Roundtrip • New York (JFK) - Chicago (ORD)JFK - ORD • Nonstop ORD - JFK • Nonstop - Swissotel - Chicago
Jul 27 - Aug 4Swissotel - Chicago + Flight
Downtown Chicago8 nights9.0/10 - Wonderful (3,349 reviews)"It was a nice room. Only complaint would be air conditioning. I don’t do hot. Hate sweating. Had turned to 65 and still not really cold. Otherwise overall nice."Reviewed May 26, 2026Roundtrip • Atlanta (ATL) - Chicago (MDW)ATL - MDW • Nonstop MDW - ATL • Nonstop - Level Chicago Fulton Market
Jul 28 - Aug 1Level Chicago Fulton Market + Flight
Downtown Chicago4 nights9.2/10 - Wonderful (489 reviews)"Amazing place"Reviewed May 26, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Sable at Navy Pier Chicago, Curio Collection by Hilton
Jul 4 - Jul 7Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago3 nights9.4/10 - Exceptional (2,516 reviews)"Clean and have a beautiful view of the lake"Reviewed May 26, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Level Chicago – Old Town
Aug 13 - Aug 16Level Chicago – Old Town + Flight
Downtown Chicago3 nights9.0/10 - Wonderful (483 reviews)"Nice and big"Reviewed May 24, 2026Roundtrip • Atlanta (ATL) - Chicago (MDW)ATL - MDW • Nonstop MDW - ATL • Nonstop
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
$188 nightly
The price is $223 total per night from Jun 3 to Jun 4
$223 total
Jun 3 - Jun 4
Total with taxes and fees
8/10 Very Good! (10,145 reviews)
"Very good location right in the heart of Downtown Chicago."
Reviewed on May 26, 2026
River Hotel
75 East Wacker Drive Chicago IL
$252 nightly
The price is $300 total per night from Jun 21 to Jun 22
$300 total
Jun 21 - Jun 22
Total with taxes and fees
8.8/10 Excellent! (5,190 reviews)
"Great location. Well-maintained. My only issue was the bathroom had a barn-style sliding door that reduced a sense of privacy, and it came off its track on my last day. The"
Reviewed on May 27, 2026
Fairmont Chicago at Millennium Park
200 North Columbus Drive Chicago IL
$374 nightly
The price is $445 total per night from Jun 14 to Jun 15
$445 total
Jun 14 - Jun 15
Total with taxes and fees
8.8/10 Excellent! (2,156 reviews)
"Stayed here for a recent trip to Chicago and overall the experience was okay. The location is convenient for downtown attractions and Millennium Park, and the hotel itself was clean and comfortable. Staff were generally polite and check-in was fairly smooth. The rooms were decent, though some areas ..."
Reviewed on May 26, 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.