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.
JW Marriott Chicago
Downtown Chicago
Save 100% on your flight
Price was $748, price is now $385 per person
$385
per person
May 17 - May 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,006 reviews)
They need to update the lobby real bad. Location is convenient a short walk to Willis Tower and you can self park very close.
Reviewed on Apr 3, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,615, price is now $987 per person
$987
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,647 reviews)
I was pleasantly surprised that the photos matched what the room would look like and especially the view. Staff and the hospitality of the hotel was excellent and I definitely would select to stay here again.
Reviewed on Apr 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
$116 nightly
The price is $137 total per night from Apr 26 to Apr 27
$137 total
Apr 26 - Apr 27
Total with taxes and fees
8/10 Very Good! (10,123 reviews)
Air conditioning did not work and was the loudest A/C I’ve ever heard in my life! Hot water didn’t work until maintenance came up and the bed was sunken in the middle. Stay away from this hotel!!!!
Reviewed on Apr 16, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $223 total per night from May 8 to May 9
$223 total
May 8 - May 9
Total with taxes and fees
8.6/10 Excellent! (2,730 reviews)
This was by far one of the worst hotel experiences of my life. The property condition is dated and not aligned with the photos. The towels had visible stains on them. The coffee maker has and old and used pod in it. The bathtub was clogged then my room wasn’t cleaned on a two night stay. I’d highly ...
Reviewed on Apr 12, 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 26 to Apr 27
$139 total
Apr 26 - Apr 27
Total with taxes and fees
8.8/10 Excellent! (1,945 reviews)
Breakfast not included. Room was very nice but had broken drawer in closet and sliding door for bathroom. No welcome with information when we arrived but room was very nice.
Reviewed on Apr 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 fascinating museums in this vibrant area.
Columbia College Chicago
4/5(127 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.
Dearborn Station
4.5/5(13 reviews)
You can learn about the history of Chicago with a visit to Dearborn Station. Experience the acclaimed theater scene and entertainment choices in this vibrant area.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
98% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% 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
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- On Leong Building
- Dearborn St Station
- Buckingham Fountain
- Second Franklin Building
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- Pontiac Building
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- 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.