South Loop Vacations from $415
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.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $980, price is now $541 per person
$541
per person
May 21 - May 24
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Room was clean, spacious, breakfast buffet was good.
Reviewed on Mar 1, 2026
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $929, price is now $564 per person
$564
per person
May 21 - May 24
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on Jan 31, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $853, price is now $535 per person
$535
per person
May 21 - May 24
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Had a great stay!! Kelly at the front desk was so sweet
Reviewed on Feb 22, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $830, price is now $522 per person
$522
per person
May 21 - May 24
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
amazing stay 10/10 would recommend
Reviewed on Feb 26, 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
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
$101 nightly
The price is $118 total per night from Mar 2 to Mar 3
$118 total
Mar 2 - Mar 3
Total with taxes and fees
8/10 Very Good! (9,897 reviews)
The amazing view of the water and park!
Reviewed on Mar 1, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $182 total per night from Apr 1 to Apr 2
$182 total
Apr 1 - Apr 2
Total with taxes and fees
8.6/10 Excellent! (2,656 reviews)
The staff was wonderful and the rooms were clean.
Reviewed on Mar 1, 2026
Hilton Garden Inn Chicago Downtown South Loop
55 E 11th Street Chicago IL
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $129 total per night from Mar 5 to Mar 6
$129 total
Mar 5 - Mar 6
Total with taxes and fees
8.8/10 Excellent! (1,872 reviews)
Such a convenient location, staff were very friendly and efficient
Reviewed on Mar 1, 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 acclaimed art scene 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.
Columbia College Chicago
Walk around the campus at Columbia College Chicago during your visit to Chicago. Discover the entertainment choices and notable monuments in this vibrant area.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
98% of travellers recommend
Chicago Bulls Basketball Game at United Center
$61
per adult
80% of travellers recommend
Explore a world of travel with Expedia
- Chicago Hotels
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- 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.