South Loop Vacations from $233
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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.
Holiday Inn Chicago - Schaumburg by IHG
Save 100% on your flight
Price was $359, price is now $233 per person
$233
per person
Apr 9 - Apr 12
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (999 reviews)
Staff was very courteous however the hotel needs to be updated. One little tiny bar of soap in the room was rather skimpy.
Reviewed on Jan 11, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was $1,825, price is now $935 per person
$935
per person
Apr 2 - Apr 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $612, price is now $353 per person
$353
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
I liked the hotel. The staff was very courteous and friendly. The room was cute. The location is fantastic.
Reviewed on Jan 20, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $766, price is now $463 per person
$463
per person
Apr 6 - Apr 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Property was clean, welcoming, pet friendly
Reviewed on Jan 18, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $520, price is now $326 per person
$326
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Room was clean, comfortable and quiet.
Reviewed on Jan 30, 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
$97 nightly
The price is $114 total per night from Feb 1 to Feb 2
$114 total
Feb 1 - Feb 2
Total with taxes and fees
8/10 Very Good! (9,826 reviews)
Awesome location
Reviewed on Jan 30, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $192 total per night from Feb 21 to Feb 22
$192 total
Feb 21 - Feb 22
Total with taxes and fees
8.4/10 Very Good! (2,590 reviews)
The room was clean and the staff was very friendly.
Reviewed on Jan 28, 2026
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
500 South Dearborn Street Chicago IL
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $109 total per night from Feb 15 to Feb 16
$109 total
Feb 15 - Feb 16
Total with taxes and fees
9.6/10 Exceptional! (1,150 reviews)
The staff was friendly, the room was really nice, the location was great. The only downfall was the low lighting in the bathroom, but that’s not a deal breaker.
Reviewed on Jan 28, 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 theater scene in this vibrant area.
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.
Dearborn St Station
You can learn about the history of Chicago with a visit to Dearborn St Station. Experience the acclaimed art scene and fascinating museums in this vibrant area.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
Chicago Bulls Basketball Game at United Center
$61
per adult
80% 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.