The Loop Vacations from $472
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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.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
Save 100% on your flight
Price was $707, price is now $472 per person
$472
per person
Aug 29 - Sep 2
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (3,935 reviews)
The best three parts were: a wonderful bed, a clean room, and a great location. This great historic hotel needs a little freshening up. Fresh paint where needed, and the hallway carpets should be cleaned or replaced. Overall, a great hotel, and I will stay there on my next trip to Chicago.
Reviewed on Jul 30, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $802, price is now $539 per person
$539
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (2,054 reviews)
Small rooms, super small sink, rough pillows, noisy A/C, and small and slow elevator.
The hotel was all about location.
Reviewed on Jul 30, 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
4 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
$145 nightly
The price is $172 total per night from Aug 30 to Aug 31
$172 total
Aug 30 - Aug 31
Total with taxes and fees
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
Fully refundableReserve now, pay when you stay
$199 nightly
The price is $236 total per night from Aug 30 to Aug 31
$236 total
Aug 30 - Aug 31
Total with taxes and fees
9/10 Wonderful! (2,698 reviews)
"The staff was very amazing and helpful. Thank you everyone there."
Reviewed on Jul 30, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$216 nightly
The price is $256 total per night from Aug 23 to Aug 24
$256 total
Aug 23 - Aug 24
Total with taxes and fees
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: Willis Tower Skydeck and The Ledge Ticket
$42
per adult
88% of travellers recommend
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.