South Loop Vacations from $501
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to $1,045 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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.
Palmer House a Hilton Hotel
Downtown Chicago
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,773 reviews)
The hotel was located close to the places we wanted to visit. Plus, it's pick up and drop off for car services was great
Reviewed on Jul 7, 2025
Virgin Hotels Chicago
Downtown Chicago
per person
Sep 27 - Oct 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
Hotel staff and room were awesome..bed very comfortable. Coffee shop was great had great fast breakfast options. Had Miss Rickie's one day was really great food. Only complaint would be the rooftop bar evening clientele...did not feel comfortable and they were loud and raucous.
Reviewed on Jul 8, 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
per person
Sep 27 - Oct 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,357 reviews)
Thank you to everyone at this amazing hotel who made our visit special. The gentleman who checked us was very nice. Special shout out to the concierge specialist, Mary who made our stay extra special. I was traveling with my two young daughters and she recommended some great activities for us to do. It did not stopped there, Mary took the time to learn my two daughter’s names and sent a special note to our room for them. It really added a special touch and really made them happy.
Reviewed on Jul 10, 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
$170 nightly
The price is $200 total per night from Aug 7 to Aug 8
$200 total
Aug 7 - Aug 8
Total includes taxes and fees
7.8/10 Good! (8,936 reviews)
"Historical place to stay if in Chicago"
Reviewed on Jul 10, 2025
Travelodge by Wyndham Downtown Chicago
65 E Harrison St, Chicago, IL
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $151 total per night from Aug 5 to Aug 6
$151 total
Aug 5 - Aug 6
Total includes taxes and fees
7/10 Good! (2,227 reviews)
"This hotel is old and needs updated. The ac is a window unit and the heater was a standalone in the room. It felt almost like and old New York City apartment. It was fairly clean however. The price was very affordable and it was only a block from the subway. The staff was excellent. The woman who ..."
Reviewed on Jul 9, 2025
Hilton Chicago
720 S Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
$209 nightly
The price is $245 total per night from Aug 4 to Aug 5
$245 total
Aug 4 - Aug 5
Total includes taxes and fees
8.4/10 Very Good! (1,984 reviews)
"The check in staff went out of their way to accommodate our combining of two separate reservations. The staff responded quickly to all our requests, and staff in general were very friendly. The room was a bit small, but this can be expected in a downtown location."
Reviewed on Jul 7, 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.
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(122 reviews)
Walk around the campus at Columbia College Chicago during your visit to Chicago. Discover the acclaimed theater scene and notable monuments in this vibrant area.
Things to do
Chicago's Dark Side Self-Guided Smartphone Walking Tour
$10
per adult
98% of travellers recommend
Field Museum of Natural History All-Access Pass
$41
per adult
Chicago Fire FC Football Game at Soldier Field
$14
per adult
Explore a world of travel with Expedia
Explore a world of travel with Expedia
- Chicago Hotels
- Hotels near Downtown Chicago
- Cheap Hotels in Chicago
- Hotels near Soldier Field
- Hotels with Free Airport Shuttle in Chicago
- Hotels near Grant Park
- Hotels near McCormick Place
- Hotels near Chicago Riverwalk
- Hotels with Free Parking in Chicago
- Extended Stay Hotels in Chicago
- Cheap Hotels in Downtown Chicago
- Hotels near Prairie District
- Hotels near Magnificent Mile
- Hotels near National Vietnam Veterans Art Museum
- Hotels near Central Station
- 5 Star Hotels in Central Station
- All-inclusive Resorts in Chicago
- Hotels near Glessner House Museum
- Hotels near Roosevelt Station
- Hotels with Suites in Chicago
- Hotels near Chicago Women's Park
- Hotels near Lollapalooza
- Hotels near Field Museum of Natural History
- Hotels near Ping Tom Memorial Park
- Hotels near William K Kimball House
- Hotels near Wintrust Arena
- Hotels near Elbridge G Keith House
- Hotels near Chicago Union Station
- Motels in Chicago
- Hotels near Near South Side
- Hotels near Chinatown
- Hotels near Chicago 18th Street Station
- Hotels near Film Row Cinema
- Hotels near The Loop
- Hotels near Millennium Park
- Hotels near Burnham Park
- 5 Star Hotels in Chicago
- Cheap Hotels in Near South Side
- Hotels near Chicago Museum Campus-11th Street Station
- Hotels with Hot Tubs in Near South Side
- Extended Stay America Hotels in Near South Side
- Hilton Hotels in Near South Side
- Motel 6 Hotels in Near South Side
- Romantic Hotels in Near South Side
- 5 Star Hotels in Near South Side
- Boutique Hotels in Near South Side
- Hotel Wedding Venues Hotels in Near South Side
- 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.