The Loop Vacations from $476
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Residence Inn by Marriott Chicago Bloomingdale
Save 100% on your flight
Price was $764, price is now $476 per person
$476
per person
Sep 23 - Sep 28
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (383 reviews)
Staff was welcoming. Continental breakfast was above average. We stayed in a 2bdr/2ba suite and just had a couple of minor annoyances with the room. The shower head was seemingly broken and there was cardboard folded and wedged in so that it would stay on the rod. If you touched it at all, it'd just fall off. The sink sprayer also did not stay up at the base of the faucet - it just dangled there in the sink. It made it a slight pain to do dishes. Neither problem was the end of the world, but attention to detail and the little things can be impacted.
Upon checking in (stayed Wed-Mon), we had asked for room cleanings (towels, bedding, and trash) for Friday and Sunday. They only did that Friday. We had to call the front desk for towels ourselves after getting back to the room from a full day of being in 100 degree weather and sweating to find we had no clean laundry.
Again, not the end of the world but it caused disappointment after having a much better experience there the year prior.
Reviewed on Jul 7, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was $2,206, price is now $1,140 per person
$1,140
per person
Sep 26 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Front desk staff was super helpful and enthusiastic. Smooth check-in, and checkout.
Reviewed on Jul 8, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,294, price is now $1,425 per person
$1,425
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
I liked everything except that the air conditioner in the hotel hallway was too cold
Reviewed on Jul 8, 2026
Kinzie Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,309, price is now $817 per person
$817
per person
Sep 26 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (2,139 reviews)
Great Staff. Super friendly and knowledgeable. Will be staying again. The beds are super comfortable.
Reviewed on Jul 9, 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
Fully refundableReserve now, pay when you stay
$206 nightly
The price is $245 total per night from Aug 6 to Aug 7
$245 total
Aug 6 - Aug 7
Total with taxes and fees
8/10 Very Good! (10,217 reviews)
"Our stay was great, best was comfortable and room was clean."
Reviewed on Jul 9, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$199 nightly
The price is $236 total per night from Aug 9 to Aug 10
$236 total
Aug 9 - Aug 10
Total with taxes and fees
8.8/10 Excellent! (5,322 reviews)
"The room we stayed in was spacious and clean. The staff were very friendly and always willing to assist guests in any way that they could. It is a prime hotel location for all activities downtown. I would stay here again, if coming back to Chicago."
Reviewed on Jul 9, 2026
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$241 nightly
The price is $287 total per night from Aug 9 to Aug 10
$287 total
Aug 9 - Aug 10
Total with taxes and fees
8.6/10 Excellent! (2,512 reviews)
"This is a very old hotel. Very well kept. Beautiful. Lots of history. So many celebs performed in the Empire Room. They have a very large lobby bar. Kind staff. Nearby restaurants all around. Location is easy to get around town 18 min walk to anything."
Reviewed on Jul 9, 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.
Stay near popular The Loop attractions
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
Explore a world of travel with Expedia
- Columbia College Chicago
- Monadnock Building
- Jane Addams' Hull-House Museum
- Wrigley Field
- Fisher Building
- Aon Center
- Chicago Cultural Center
- Richard J. Daley Center
- Roosevelt University
- Cibc Theatre
- Cna Center
- United Center
- Crown Fountain
- Merchandise Mart
- Skydeck Ledge
- Marina City
- Richard Norton Gallery
- St. James Cathedral
- Art Institute of Chicago
- Old Colony Building
- Gen. John Logan Memorial
- Chicago Loop Synagogue
- Fourth Presbyterian Church
- Shops at North Bridge
- Santa Fe Building
- Millennium Park
- Chicago Board of Trade Building
- Tribune Tower
- Amazing Chicago's Funhouse Maze
- Chicago Museum Campus Vacations
- Sullivan Center
- Chicago Place Mall
- Picasso Statue
- International Museum of Surgical Science
- Ronald McDonald House near Lurie Children’s
- Chase Tower
- University of Illinois Chicago
- Harold Washington Library Center
- North Avenue Beach
- Buckingham Fountain
- Unity Temple
- The East Bank Club
- Water Tower Place
- 333 West Wacker Drive
- Ohio Street Beach
- Grant Park
- 311 S Wacker Dr
- Ann and Robert H. Lurie Children's Hospital
- Chicago Children's Museum
- Bridgehouse and Chicago River Museum
- Chicago City Hall
- Rookery
- Cloud Gate
- Magnificent Mile Vacations
- House of Blues Chicago
- Chicago Water Tower
- Marshall Field Building
- Lincoln Park Zoo
- Michigan Avenue Bridge
- Civic Opera House
- Cadillac Palace Theatre
- Lincoln Park Conservatory
- Bally's Casino Chicago
- State Street
- Chicago Vacations
- Goodman Theater
- Michigan Avenue
- Robie House
- Driehaus Museum
- The Salt Shed
- Navy Pier
- Ping Tom Memorial Park
- Oak Street Beach
- Film Row Cinema
- Chicago Architecture Foundation
- Marquette Building
- Daley Plaza
- Willis Tower
- Chicago History Museum
- Pontiac Building
- 900 North Michigan Shops
- Northwestern Memorial Hospital
- Holy Name Cathedral
- Carbide and Carbon Building
- Chicago Riverwalk
- Chicago Symphony Orchestra
- Auditorium Building and Theatre
- Montrose Beach
- Cooking & Hospitality Institute of Chicago
- Maggie Daley Park
- Haskell Building
- Depaul University-Loop Campus
- Downtown Chicago Vacations
- Dave & Buster's
- Chicago Temple
- River North Vacations
- Theatre District Vacations
- Symphony Center
- Wrigley Building
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.