South Loop Vacations from $148
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.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was $654, price is now $254 per person
$254
per person
Feb 9 - Feb 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
The room was beautiful and clean and a good city view of the city
Reviewed on Nov 26, 2025
The Emily Hotel
Downtown Chicago
Price was $776, price is now $384 per person
$384
per person
Feb 9 - Feb 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.
Reviewed on Nov 26, 2025
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $859, price is now $437 per person
$437
per person
Feb 17 - Feb 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Staff was friendly and outgoing throughout our 2 night stay. Roome were very clean, spacious with floor to ceiling windows and large walk-in showers. Bottle of wine upon check-in.
Reviewed on Nov 25, 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
$104 nightly
The price is $122 total per night from Dec 22 to Dec 23
$122 total
Dec 22 - Dec 23
Total with taxes and fees
8/10 Very Good! (9,671 reviews)
Nice staff & clean room
Reviewed on Nov 29, 2025
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $154 total per night from Dec 20 to Dec 21
$154 total
Dec 20 - Dec 21
Total with taxes and fees
8.4/10 Very Good! (2,323 reviews)
Room was great. Staff was very helpful. I would recommend to anyone….
Reviewed on Nov 28, 2025
Homewood Suites by Hilton Chicago Downtown South Loop
59 E. 11th Street Chicago IL
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $102 total per night from Dec 7 to Dec 8
$102 total
Dec 7 - Dec 8
Total with taxes and fees
8.6/10 Excellent! (2,138 reviews)
Awesome very clean & nice
Reviewed on Nov 24, 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 fascinating museums in this vibrant area.
Columbia College Chicago
4/5(122 reviews)
Walk around the campus at Columbia College Chicago during your visit to Chicago. Discover the entertainment choices and notable monuments in this vibrant area.
Dearborn St Station
4.5/5(13 reviews)
You can learn about the history of Chicago with a visit to Dearborn St Station. Experience the acclaimed art scene and entertainment choices in this vibrant area.
Things to do
Chicago Bulls Basketball Game at United Center
$98
per adult
80% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$45
per adult
94% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
84% 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.