South Loop Vacations from $274
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.
Holiday Inn Express & Suites Zion by IHG
Save 100% on your flight
Price was $392, price is now $274 per person
$274
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (188 reviews)
Staff was Excellent! Room was super clean!
Reviewed on Feb 20, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,409, price is now $862 per person
$862
per person
May 26 - May 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Interesting property in that it is a high rise building of furnished suites with certain floors available as a “hotel”. Coffee shop, gym and lounge are all nice as are the suites. Just know this is not a service oriented hotel experience. No doorman, uniformed person at desk, room or maid service etc.
Reviewed on Mar 14, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $641, price is now $417 per person
$417
per person
Apr 17 - Apr 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Riu Chicago was a wonderful hotel. Room was clean and spacious. Breakfast was an added bonus. Within walking distance to many restaurants and stores.
Reviewed on Mar 17, 2026
Wind Creek Southland Casino and Hotel
East Hazel Crest
Save 100% on your flight
Price was $796, price is now $561 per person
$561
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (MDW)
9.4/10 Exceptional! (278 reviews)
Everything that i saw and used was great
Reviewed on Mar 16, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was $775, price is now $550 per person
$550
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
The room was clean, comfortable, and well organized The location was perfect, close to restaurants and attractions
Reviewed on Mar 15, 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
$113 nightly
The price is $133 total per night from Apr 1 to Apr 2
$133 total
Apr 1 - Apr 2
Total with taxes and fees
8/10 Very Good! (9,951 reviews)
The condition of the halls of the hotel and building in general showed its age, but the room had been updated and was clean. The sink and tub drainage was poor. The room was heated very well especially on a cold day. The front desk lady that checked me in seemed in a foul mood but I am sure with ...
Reviewed on Mar 17, 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! (2,692 reviews)
Love the amenities. Convenient location close to everything we needed. Beautiful hotel.
Reviewed on Mar 17, 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! (1,913 reviews)
Hotel was clean, up to date, afforable when compared to other hotels in the area and conveniently located. These are the best parts of this Hilton nother else really sticks out about it. There is a bar and restaurant attached to the hotel and a bakery at the corner of the same block if youre in town ...
Reviewed on Mar 16, 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.
Columbia College Chicago
Walk around the campus at Columbia College Chicago during your visit to Chicago. Discover the acclaimed art scene and notable monuments in this vibrant area.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
98% of travellers recommend
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- 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
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- 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.