South Loop Vacations from $791
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 Riu Plaza Chicago
Downtown Chicago
Price was $1,614, price is now $791 per person
$791
per person
Jun 21 - Jun 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
This is a gem. The staff were caring, welcoming and accommodating. The property is at a perfect location with many eating and shopping options. The bus stop was feet away and access to the metro a couple blocks away.
Breakfast was great; it had a great selection of food.
Negative: I tried modifying my reservation a couple weeks prior my stay, after noticing a mistake made at the time of booking. However, I was unable to reach anyone at tye hotel, over the phone. Later, I was told by the site I booked my stay, that the hotel denied the request.
I will definitely go back to this hotel!
Reviewed on Apr 5, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $1,582, price is now $873 per person
$873
per person
Jun 21 - Jun 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
Enjoyed our stay, will definitely be back
Reviewed on Apr 5, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,593, price is now $913 per person
$913
per person
Jun 11 - Jun 16
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
Room was super clean. The view all the way down to the lake from balcony was nice.
Reviewed on Apr 2, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,783, price is now $1,076 per person
$1,076
per person
Jun 21 - Jun 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,647 reviews)
Clean room! The view was amazing
Reviewed on Apr 6, 2026
Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,261, price is now $801 per person
$801
per person
Jun 21 - Jun 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,357 reviews)
Great location. Staff was welcoming. Room could have been cleaned better hair on sink, toilet and bed but overall not the worse I’ve seen. Would stay again for sure.
Reviewed on Apr 5, 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
$110 nightly
The price is $129 total per night from Apr 16 to Apr 17
$129 total
Apr 16 - Apr 17
Total with taxes and fees
8/10 Very Good! (10,046 reviews)
Property is always well maintained, very clean and tidy
Reviewed on Apr 6, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$196 nightly
The price is $231 total per night from Apr 26 to Apr 27
$231 total
Apr 26 - Apr 27
Total with taxes and fees
8.6/10 Excellent! (2,724 reviews)
Didn't get the room I reserved (2 months ago), which was 2 double beds. Instead gave me a king (for 2 adults and a child). What's the point of a reservation if they're just going to give my room away? Easter weekend, hotel full of young teenage girls, who instead of acting like young ladies, were ...
Reviewed on Apr 5, 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 13 to Apr 14
$139 total
Apr 13 - Apr 14
Total with taxes and fees
8.8/10 Excellent! (1,949 reviews)
Staff and service was great. I’ve stayed here every year since 2020 and I love it.
Reviewed on Apr 5, 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 entertainment choices 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.