South Loop Vacations from $390
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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.
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $664, price is now $390 per person
$390
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
The staff was the best part of the hotel, accommodating, polite and patient. Rooms were so so but they offer so many amenities that is more than makes up for it
Reviewed on Apr 14, 2026
Baymont By Wyndham Schaumburg Chicago Northwest
Save 100% on your flight
Price was $897, price is now $464 per person
$464
per person
May 18 - May 22
found 14 hours ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
No reviews
Everyone was nice, room was what i expected, and the late checkout policy was helpful and clear and easy to approach.
Reviewed on Apr 11, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $864, price is now $460 per person
$460
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
Great stay! Loved to come back. Friendly staff!
Reviewed on Apr 13, 2026
JW Marriott Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,066, price is now $569 per person
$569
per person
May 16 - May 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,004 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
Level Chicago – Old Town
Downtown Chicago
Price was $1,613, price is now $917 per person
$917
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
This property never disappoints! The staff are awesome, particularly Nu at the front desk! Always very pleasant and friendly, provides awesome service every time we visit!
Reviewed on Apr 13, 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! (10,144 reviews)
We stayed here in order to be close to the Auditorium for our concert. The price is great, but you get what you pay for. It was very average, which isn't a bad thing necessarily. My only big comlaint is the lack of individualized climate control. There is a unit and you are at the mercy of whatever ...
Reviewed on Apr 14, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
$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! (2,735 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
$114 nightly
The price is $134 total per night from Apr 26 to Apr 27
$134 total
Apr 26 - Apr 27
Total with taxes and fees
8.8/10 Excellent! (1,954 reviews)
Yes
Reviewed on Apr 14, 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.
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 fascinating museums.
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.
Things to do
Chicago Bulls Basketball Game at United Center
$66
per adult
80% 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
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- On Leong Building
- Dearborn St Station
- Buckingham Fountain
- Second Franklin Building
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- 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.