South Loop Vacations from $330
Book a Hotel + Flight or Car together to unlock savings
Your South Loop Vacation
Cafes, bars and pubs and history are just the start of the things waiting for you when you lock in a vacation package to South Loop. Whether you're craving adventure, relaxation or something else, this commercial neighborhood is likely to have it. Not sure what to see and do during your trip to South Loop? Nearby attractions such as Millennium Park, Willis Tower and Art Institute of Chicago are good places to begin. Expedia will help you turn your ideal South Loop vacation into reality, whatever your budget or travel plans.
The Latest South Loop Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago
Downtown Chicago
Price was $473, price is now $330 per person
$330
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything.
Reviewed on Nov 3, 2026
Pendry Chicago
Downtown Chicago
Price was $704, price is now $483 per person
$483
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.
Reviewed on Nov 8, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $510, price is now $355 per person
$355
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
Really enjoyed my stay! In a walkable location to many attractions. Breakfast was great.
Reviewed on Nov 10, 2026
Where to stay in South Loop
Find the best South Loop areas and neighborhoods for the activities you enjoy most. Learn more about South Loop
Downtown Chicago
4 out of top 10 points of interest in this area
Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
South Loop Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $127 total per night from Nov 22 to Nov 23
$127 total
Nov 22 - Nov 23
Total with taxes and fees
8/10 Very Good! (10,163 reviews)
"Love that this is a classic Chicago downtown hotel experience! The lobby area is such a throwback to a different era in Chicago, which is cool. The rooms (we were in 933) are in desperate need of an upgrade by whatever parent company owns this hotel. The bathroom was severely outdated with a bathroom ..."
Reviewed on Nov 10, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$162 nightly
The price is $190 total per night from Nov 27 to Nov 28
$190 total
Nov 27 - Nov 28
Total with taxes and fees
Sentral Michigan Avenue
808 SOUTH MICHIGAN AVENUE Chicago IL
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $219 total per night from Nov 12 to Nov 13
$219 total
Nov 12 - Nov 13
Total with taxes and fees
9/10 Wonderful! (1,411 reviews)
"Great views but rooms need better cleaning and maintenance."
Reviewed on Nov 10, 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 South Loop attractions
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Explore a world of travel with Expedia
- Best Western Hotels in South Loop
- Chinatown Hotels
- Motels in Chicago
- Cabins in Chicago
- Motel 6 Hotels in Near South Side
- 5 Star Hotels in Chicago
- Free Airport Transportation in Chicago
- Downtown Chicago Hotels
- The Loop Hotels
- Hotels in Chicago
- 4 Star Hotels in Chicago
- Near South Side Hotels
- Budget Hotels in South Loop
- South Loop Hotels
- Delta Air Lines Atlanta (ATL) to Chicago (MDW) flights
- Flights to Chicago
- Flights to Evanston
- Porter Airlines Toronto (YTZ) to Chicago (MDW) flights
- Flights to Oak Park
- Flights from Los Angeles (LAX) to Chicago (MDW)
- Flights to Bridgeview
- Flights to Midway Intl.
- Flights to Berwyn
- Flights from Atlanta (ATL) to Chicago (MDW)
- Visit South Loop
- Where to stay in Central Chicago
- Chicago Vacations
- Central Chicago All Inclusive Vacation Packages
- Central Chicago All Inclusive Vacation Packages
- Chicago All Inclusive Vacation Packages
- Central Chicago All Inclusive Vacation Packages
- Bellwood Vacations
- Chicago All Inclusive Vacation Packages
- Chicago All Inclusive Vacation Packages
- Rosemont Vacations
- Chicago All Inclusive Vacation Packages
- Grant Park
- Where to stay in Oakbrook Terrace
- Where to stay in Cicero
- Where to stay in Evanston
- Downtown Chicago Vacations
- Where to stay in Bridgeview
- Central Chicago All Inclusive Vacation Packages
- Visit Rush Street
- Bensenville Vacations
- Visit Printers Row
- Chicago All Inclusive Vacation Packages
- Where to stay in Rosemont
- Art Institute of Chicago
- Oak Park Vacations
- Where to stay in Oak Park
- Central Chicago All Inclusive Vacation Packages
- Chicago All Inclusive Vacation Packages
- Summit Vacations
- Blue Island Vacations
- Westchester Vacations
- Visit United Center
- Visit Chicago
- Visit Downtown Chicago
- Visit Streeterville
- Chicago Cultural Center
- Where to stay in Chicago
- Visit Lincoln Park
- Where to stay in North Pullman
- Willis Tower
- Visit Magnificent Mile
- Visit The Loop
- Where to stay in South Side
- Visit West Loop
- Darien Vacations
- Car rentals near Central Station
- Hertz Rental Cars in South Loop
- Budget Rental Cars in Chicago
- Enterprise Rental Cars in Chicago
- Car rentals near South Loop
- Car rentals near The Loop
- SUV Car Rentals in Chicago
- Car rentals near Magnificent Mile
- Car rentals near Chicago
- Minivan Car Rentals in Chicago
- Car rentals near Downtown Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.