South Loop Vacations from $237
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 - Schaumburg by IHG
Save 100% on your flight
Price was $447, price is now $237 per person
$237
per person
Dec 26 - Dec 31
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
16.4/10 Exceptional! (999 reviews)
Rooms were clean and overall the hotel was nice
Reviewed on Nov 1, 2025
Level Chicago – Old Town
Downtown Chicago
Price was $3,257, price is now $1,529 per person
$1,529
per person
Dec 28 - Jan 3
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
18/10 Exceptional! (380 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.
Reviewed on Nov 9, 2025
The Westin Michigan Avenue Chicago
Downtown Chicago
Save 100% on your flight
Price was $970, price is now $486 per person
$486
per person
Dec 20 - Dec 23
found 6 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
17.6/10 Exceptional! (1,075 reviews)
I didn’t have breakfast. Just coffee from the Starbucks kiosk.
Reviewed on Nov 17, 2025
Wind Creek Southland Casino and Hotel
East Hazel Crest
Save 100% on your flight
Price was $743, price is now $400 per person
$400
per person
Dec 26 - Dec 31
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (MDW)
18.8/10 Exceptional! (160 reviews)
Everything was great
Reviewed on Nov 19, 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
4 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
$110 nightly
The price is $129 total per night from Nov 24 to Nov 25
$129 total
Nov 24 - Nov 25
Total with taxes and fees
8/10 Very Good! (9,603 reviews)
Room had a beautiful view, seemed fairly modern and clean. All staff was pleasant and helpful. The hotel itself is conveniently situated, with access to key amenities and attractions.
Reviewed on Nov 18, 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 Nov 26 to Nov 27
$154 total
Nov 26 - Nov 27
Total with taxes and fees
8.4/10 Very Good! (2,304 reviews)
Good location, easily walkable
Reviewed on Nov 18, 2025
Travelodge by Wyndham Downtown Chicago
65 E Harrison St Chicago IL
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $108 total per night from Dec 9 to Dec 10
$108 total
Dec 9 - Dec 10
Total with taxes and fees
7.2/10 Good! (2,463 reviews)
Yes. It’s really good
Reviewed on Nov 17, 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
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
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
Skydeck - Willis Tower Admission
$44
per adult
98% 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.