South Loop Vacations from $470
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 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 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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $719, price is now $470 per person
$470
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,604 reviews)
Great experience and friendly staff
Reviewed on Apr 6, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $985, price is now $525 per person
$525
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
The room was clean. Very modern hotel. Great service and staff. Great experience overall.
Reviewed on Apr 7, 2026
Hilton Chicago O'Hare Airport
O'Hare
Save 100% on your flight
Price was $796, price is now $497 per person
$497
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (2,241 reviews)
Great location and service. Needs alittle renovation of interior
Reviewed on Apr 7, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Save 100% on your flight
Price was $1,591, price is now $1,008 per person
$1,008
per person
Jun 11 - Jun 16
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,332 reviews)
The Thompson Chicago is a wonderful boutique Hotel located in the perfect part of the city.
Reviewed on Apr 6, 2026
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,036, price is now $679 per person
$679
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,123 reviews)
The staff at the Pendry are top notch. We arrived early and just wanted to drop our bags off, but the staff was able to check us in several hours early. Upon learning it was my birthday, the bell hop brought me a glass of wine from the bar and later, the staff sent up a bottle of prosecco and birthday cupcakes. Our room
Reviewed on Apr 7, 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
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.
South Loop Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $137 total per night from Apr 26 to Apr 27
$137 total
Apr 26 - Apr 27
Total with taxes and fees
8/10 Very Good! (10,060 reviews)
Great location but very old and run down..needs updates
Reviewed on Apr 7, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $221 total per night from May 8 to May 9
$221 total
May 8 - May 9
Total with taxes and fees
8.6/10 Excellent! (2,717 reviews)
It was a great hotel!
Reviewed on Apr 7, 2026
Hilton Garden Inn Chicago Downtown South Loop
55 E 11th Street Chicago IL
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $139 total per night from Apr 26 to Apr 27
$139 total
Apr 26 - Apr 27
Total with taxes and fees
8.8/10 Excellent! (1,950 reviews)
Stay was great
Reviewed on Apr 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 South Loop
Lollapalooza
After visiting Lollapalooza, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.
Gen. John Logan Memorial
Set on a grassy mound in a quiet corner of Grant Park, this equestrian statue celebrates an American Civil War hero and faithful servant of Abraham Lincoln.
Ping Tom Memorial Park
After visiting Ping Tom Memorial Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.
Things to do
Chicago Bulls Basketball Game at United Center
$66
per adult
80% of travellers recommend
Explore a world of travel with Expedia
- Chicago Hotels
- Hotels near Downtown Chicago
- Cheap Hotels in Chicago
- Hotels near Soldier Field
- Hotels with Free Airport Shuttle in Chicago
- Hotels near Grant Park
- Hotels near McCormick Place
- Hotels near Chicago Riverwalk
- Hotels with Free Parking in Chicago
- Extended Stay Hotels in Chicago
- Cheap Hotels in Downtown Chicago
- Hotels near Prairie District
- Hotels near Magnificent Mile
- Hotels near National Vietnam Veterans Art Museum
- Hotels near Central Station
- 5 Star Hotels in Central Station
- All-Inclusive Resorts in Chicago
- Hotels near Glessner House Museum
- Hotels near Roosevelt Station
- Hotels with Suites in Chicago
- Hotels near Chicago Women's Park
- Hotels near Lollapalooza
- Hotels near Field Museum of Natural History
- Hotels near Ping Tom Memorial Park
- Hotels near William K Kimball House
- Hotels near Wintrust Arena
- Hotels near Elbridge G Keith House
- Hotels near Chicago Union Station
- Motels in Chicago
- Hotels near Near South Side
- Hotels near Chinatown
- Hotels near Chicago 18th Street Station
- Hotels near Film Row Cinema
- Hotels near The Loop
- Hotels near Millennium Park
- Hotels near Burnham Park
- 5 Star Hotels in Chicago
- Cheap Hotels in Near South Side
- Hotels near Chicago Museum Campus-11th Street Station
- Hotels with Hot Tubs in Near South Side
- Extended Stay America Hotels in Near South Side
- Hilton Hotels in Near South Side
- Motel 6 Hotels in Near South Side
- Romantic Hotels in Near South Side
- 5 Star Hotels in Near South Side
- Boutique Hotels in Near South Side
- Hotel Wedding Venues Hotels in Near South Side
- Adults Only Resorts & in Near South Side
- Chicago Vacations
- Visit Downtown Chicago
- Soldier Field
- National Vietnam Veterans Art Museum
- Field Museum of Natural History
- Glessner House Museum
- Ping Tom Memorial Park
- Olmec Head No 8
- William K Kimball House
- Mccormick Place
- Joseph G Coleman House
- Adler Planetarium and Astronomy Museum
- Elbridge G Keith House
- Grant Park
- Film Row Cinema
- Burnham Park
- Wintrust Arena
- Gen. John Logan Memorial
- On Leong Building
- Dearborn St Station
- Buckingham Fountain
- Second Franklin Building
- Visit Central Station
- Visit Chicago
- University of Illinois Chicago
- Chicago Museum Campus Vacations
- Chinatown Vacations
- Willis Tower
- Lollapalooza
- Columbia College Chicago
- Art Institute of Chicago
- Harold Washington Library Center
- Pontiac Building
- American Police Center & Museum
- Roosevelt University
- Visit Near South Side
- Auditorium Building and Theatre
- Maxwell Street Market
- Where to stay in Chicago
- Copernicus Statue
- Arie Crown Theater
- Northerly Island Natural Area
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.