South Loop Vacations from $437
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 Chicago North-Evanston by IHG
Downtown Evanston
Price was $629, price is now $437 per person
$437
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,818 reviews)
I love this hotel. Check-in was pleasant, efficient, and the hotel's amenities were nicely highlighted. I was blessed to be granted a room on the south side ofbthe building
Reviewed on Mar 31, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,056, price is now $651 per person
$651
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Hotel is in a good central location near many of the main attractions. Room was spacious and clean. Nice bar downstairs, there is also a rooftop bar, but that is only open in after Easter in summer.
Buffet breakfast is included and that makes it very good value. Hotel also has a gym/
Not too many amenities in the room though.
Reviewed on Apr 2, 2026
Arlo Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,394, price is now $940 per person
$940
per person
Jun 21 - Jun 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,019 reviews)
Wonderful location Nicely updated and appointed rooms. Quiet. Quick elevator. Excellent restaurant on site. Great value for money. Very helpful staff.
Reviewed on Mar 29, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,379, price is now $952 per person
$952
per person
Jun 21 - Jun 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,862 reviews)
Nice staff, clean rooms, however elevator is slow
Reviewed on Apr 2, 2026
Illinois Beach Hotel
Price was $623, price is now $445 per person
$445
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8/10 Very Good! (504 reviews)
Waited 15min to check in. Received an apology along with an explanation of having to do three jobs at once. Shower ceiling had peeling paint with mildew/mold stains. Vanity would not drain. Was relocated to another RM.
Reviewed on Apr 1, 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
$107 nightly
The price is $125 total per night from Apr 5 to Apr 6
$125 total
Apr 5 - Apr 6
Total with taxes and fees
8/10 Very Good! (10,007 reviews)
Good location for where we needed to be in the city. It’s a very dated hotel.
Reviewed on Apr 2, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$194 nightly
The price is $228 total per night from Apr 5 to Apr 6
$228 total
Apr 5 - Apr 6
Total with taxes and fees
8.6/10 Excellent! (2,715 reviews)
The hotel is great for families of all ages!
Reviewed on Apr 3, 2026
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
500 South Dearborn Street Chicago IL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $149 total per night from Apr 26 to Apr 27
$149 total
Apr 26 - Apr 27
Total with taxes and fees
9.6/10 Exceptional! (1,226 reviews)
I loved this hotel. Very classy, well decorated combining the historic aspects of the area with the buildings original high quality finishings and making it all look seamless. With that said, the view was only that of a nearby brick building but it did keep it much more quiet. They even had earplugs ...
Reviewed on Apr 2, 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 entertainment choices.
Things to do
Chicago Bulls Basketball Game at United Center
$66
per adult
80% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% 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
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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.