The Loop Vacations
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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.
Price found within the past 48 hours. Click for updated prices.
- Hollywood Casino Aurora
Jul 27 - Jul 30Hollywood Casino Aurora + Flight
Aurora3 nightsRoundtrip • Atlanta (ATL) - Chicago (MDW)ATL - MDW • Nonstop MDW - ATL • Nonstop$1,531$392found 1 day agoper traveler - Level Chicago Fulton Market
Aug 21 - Aug 25Level Chicago Fulton Market + Flight
Downtown Chicago4 nights9.2/10 - Wonderful (492 reviews)"Fully equipmet"Reviewed June 2, 2026Roundtrip • Atlanta (ATL) - Chicago (MDW)ATL - MDW • Nonstop ORD - ATL • Nonstop - Hotel Riu Plaza Chicago
Aug 28 - Aug 31Hotel Riu Plaza Chicago + Flight
Downtown Chicago3 nights9.4/10 - Exceptional (4,330 reviews)"Great rooftop bar and breakfast."Reviewed June 3, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Level Chicago – Old Town
Aug 21 - Aug 25Level Chicago – Old Town + Flight
Downtown Chicago4 nights9.0/10 - Wonderful (488 reviews)"Very clean and loved the location and amenities with the store on the first floor was fantastic"Reviewed June 3, 2026Roundtrip • Atlanta (ATL) - Chicago (MDW)ATL - MDW • Nonstop ORD - ATL • Nonstop - Hotel Saint Clair- Magnificent Mile
Aug 8 - Aug 23Hotel Saint Clair- Magnificent Mile + Flight
Downtown Chicago15 nights8.4/10 - Very Good (1,956 reviews)"Clean room to stay."Reviewed June 2, 2026Roundtrip • Dallas (DFW) - Chicago (ORD)DFW - ORD • Nonstop ORD - DFW • 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
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $168 total per night from Jun 29 to Jun 30
$168 total
Jun 29 - Jun 30
Total with taxes and fees
8/10 Very Good! (10,164 reviews)
"The location was excellent. Close to all the museums, shopping district and river walk."
Reviewed on Jun 3, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $181 total per night from Jul 5 to Jul 6
$181 total
Jul 5 - Jul 6
Total with taxes and fees
8.8/10 Excellent! (5,230 reviews)
"n/a"
Reviewed on Jun 3, 2026
Fairmont Chicago at Millennium Park
200 North Columbus Drive Chicago IL
Fully refundableReserve now, pay when you stay
$209 nightly
The price is $249 total per night from Jul 1 to Jul 2
$249 total
Jul 1 - Jul 2
Total with taxes and fees
8.8/10 Excellent! (2,173 reviews)
"My room was old and the paint in the bathroom was peeling"
Reviewed on Jun 3, 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
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.
Art Institute of Chicago
Explore a massive collection of works celebrating different cultures and historical times, from ancient Egypt to modern installations.
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
$174
per adult
80% 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.