The Loop Vacations from $349
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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.
Hilton Chicago
Downtown Chicago
Save 100% on your flight
Price was $538, price is now $349 per person
$349
per person
Apr 1 - Apr 4
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (2,301 reviews)
Th staff was mostly helpful, Jennifer that was in charge of the pool fitness area was very helpful, she gave us information on family restaurants cheap close to the hotel to eat at the first night we were in town, she was a gem, the hotel itself needs a lot of work, the windows in the room we stayed in were very drafty and we had issues keeping the room warm, the surprise costs was a shock to us, they don’t disclose the fact that they charge the paying guests at the hotel to park in the garage, the fact that they charge guests to use the pool and the fitness areas is just crazy, the pool area and hot tubs were not anything special and most hotels do not charge guests to use the amenities, we won’t be staying with the Hilton anywhere in the USA again even if we are given free room, we just weren’t impressed, it was just a basic hotel to us,
Reviewed on Jan 6, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $736, price is now $433 per person
$433
per person
Apr 1 - Apr 4
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The staff and hotel were great. The rooms were spacious and bathrooms were very well thought out to accommodate multiple people. The staff were friendly and helpful. The breakfast every morning was wonderful. The breakfast has everything you can imagine. Will definitely stay there again.
Reviewed on Jan 7, 2026
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $659, price is now $403 per person
$403
per person
Apr 1 - Apr 4
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Perfect location, comfortable and clean room
Reviewed on Jan 5, 2026
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination
Save 100% on your flight
Price was $590, price is now $371 per person
$371
per person
Feb 13 - Feb 15
found 12 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.4/10 Very Good! (999 reviews)
Enjoyed the room. The staff could use a hug not the friendliest. The games our outdated. Seen many guest besides me decide to go play at the other area casino
Reviewed on Jan 1, 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
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$168 nightly
The price is $192 total per night from Jan 14 to Jan 15
$192 total
Jan 14 - Jan 15
Total with taxes and fees
8.4/10 Very Good! (2,226 reviews)
Room was very clean and staff was great
Reviewed on Jan 6, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $192 total per night from Jan 14 to Jan 15
$192 total
Jan 14 - Jan 15
Total with taxes and fees
8.4/10 Very Good! (2,501 reviews)
Everything was amazing abt my stay
Reviewed on Jan 7, 2026
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $103 total per night from Jan 30 to Jan 31
$103 total
Jan 30 - Jan 31
Total with taxes and fees
8.6/10 Excellent! (2,047 reviews)
Pedro and front office staff made our stay excellent. Return customer love the location, room quality and value overall. Room size and features make this our first choice in the city
Reviewed on Jan 7, 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.
Willis Tower
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
100% of travellers recommend
Chicago Bulls Basketball Game at United Center
$83
per adult
80% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% 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.