South Loop Vacations from $179
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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 $306, price is now $179 per person
$179
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,273 reviews)
Comfortable
Friendly
Reviewed on Oct 20, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $779, price is now $420 per person
$420
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.
Reviewed on Oct 16, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $787, price is now $429 per person
$429
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Very gracious staff, impressive breakfast offerings/venue, cleanliness, location, Rooftop Bar, and seasonal (Halloween) decorations.
Reviewed on Oct 20, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $739, price is now $410 per person
$410
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The kitchen was VERY clean and very well stocked. Our room was as nice as any room as I have ever stayed in. The Hotel Manager and Pablo, the Director of Rooms, were outstanding!!! they were truly a credit to the Trump brand. I have stayed at the Trump International and would stay there again in a heartbeat.
Reviewed on Oct 20, 2025
Hampton Inn & Suites Chicago Medical District UIC
Near West Side
Save 100% on your flight
Price was $338, price is now $190 per person
$190
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (281 reviews)
Staff were very nice, breakfast included and lots of fast casual dining nearby, 10-min walk to metro, otherwise location is a little drab and remote. Tub in bathroom had some chipped paint but otherwise the room was spacious and clean.
Reviewed on Oct 17, 2025
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
$145 nightly
The price is $170 total per night from Nov 2 to Nov 3
$170 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (9,498 reviews)
"The website for the gazebo restaurant within the hotel said there was an extensive menu. When you get down to the place it’s a small buffett set up which was similar to any other continental breakfast with some cereal, muffins, fruit, some biscuits, bacon and sausage etc. There was also a man at ..."
Reviewed on Oct 20, 2025
Hilton Chicago
720 S Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
$209 nightly
The price is $245 total per night from Oct 30 to Oct 31
$245 total
Oct 30 - Oct 31
Total with taxes and fees
8.4/10 Very Good! (2,276 reviews)
"Just one complaint, the rooms can use a makeover, especially the carpet."
Reviewed on Oct 19, 2025
Travelodge by Wyndham Downtown Chicago
65 E Harrison St, Chicago, IL
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $111 total per night from Nov 16 to Nov 17
$111 total
Nov 16 - Nov 17
Total with taxes and fees
7.2/10 Good! (2,426 reviews)
"Location to theater"
Reviewed on Oct 19, 2025
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 theater scene in this vibrant area.
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 entertainment choices.
Columbia College Chicago
4/5(122 reviews)
Walk around the campus at Columbia College Chicago during your visit to Chicago. Discover the fascinating museums and notable monuments in this vibrant area.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
$45
per adult
100% of travellers recommend
Explore a world of travel with Expedia
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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
- Willow Creek Chicago
- 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.