The Loop Vacations from $645
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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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,091, price is now $645 per person
$645
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,809 reviews)
decent property - definitely shows better in photos. that was probably my biggest let-down. also, only staying one night, the room cleaner came into our room at 8 am despite check out time not being until noon. my kid was still asleep and I was in the shower. front desk service level definitely elevated the rating.
Reviewed on Jul 17, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,237, price is now $751 per person
$751
per person
Sep 25 - Sep 29
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place.
Reviewed on Jul 14, 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
$210 nightly
The price is $250 total per night from Aug 10 to Aug 11
$250 total
Aug 10 - Aug 11
Total with taxes and fees
8/10 Very Good! (10,194 reviews)
"When we made the reservation in April for July we requested a view, high floor, away from elevator and two extra pillows. We got floor 11 of 14 so pretty good. No view-looking across to other room, no extra pillows, elevator behind king room wall. A/c was horrible, 1st room of suite was 74 degree ..."
Reviewed on Jul 17, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$174 nightly
The price is $207 total per night from Jul 19 to Jul 20
$207 total
Jul 19 - Jul 20
Total with taxes and fees
8.8/10 Excellent! (5,316 reviews)
"Staff was helpful"
Reviewed on Jul 17, 2026
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
$281 nightly
The price is $334 total per night from Aug 9 to Aug 10
$334 total
Aug 9 - Aug 10
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: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% 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.