South Loop Vacations from $156
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.
Illinois Beach Hotel
Save 100% on your flight
Price was $261, price is now $156 per person
$156
per person
Oct 30 - Nov 2
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.2/10 Very Good! (384 reviews)
I like the place, it is very quiet and safe, but the room requires better cleaning, the balcony was not clean and blinds need to be washed, anyhow i liked it.
Reviewed on Aug 21, 2025
The Emily Hotel
Downtown Chicago
Price was $1,322, price is now $641 per person
$641
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend.
Also the coffee bags ? PERFECTION. Just had to add that
Reviewed on Aug 22, 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,030, price is now $596 per person
$596
per person
Nov 10 - Nov 16
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.
Reviewed on Aug 21, 2025
Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $999, price is now $599 per person
$599
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,020 reviews)
Overall is good but 1 concern we encountered is there is a clicking sound in our room or near our room, that distracts my husband while sleeping.
Reviewed on Aug 24, 2025
Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,030, price is now $621 per person
$621
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (3,059 reviews)
Loved the property, big size room and very cool decoration! Great location
Reviewed on Aug 22, 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
$143 nightly
The price is $168 total per night from Aug 25 to Aug 26
$168 total
Aug 25 - Aug 26
Total with taxes and fees
7.8/10 Good! (8,996 reviews)
Great view! Safe location for food music and park
"Got a very good rate during an event that had filled up many nearby hotels. Lovely sparkling-clean room, rather small, a firm king bed, dresser, & table. It felt cozy, not crowded, enough drawers and closet space, nice-size bathroom with shower-tub. Room has nice ornate details. 10th-floor sunrise ..."
Reviewed on Aug 24, 2025
Hilton Chicago
720 S Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $194 total per night from Sep 2 to Sep 3
$194 total
Sep 2 - Sep 3
Total with taxes and fees
8.4/10 Very Good! (2,105 reviews)
"Nice"
Reviewed on Aug 22, 2025
Travelodge by Wyndham Downtown Chicago
65 E Harrison St, Chicago, IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $136 total per night from Sep 2 to Sep 3
$136 total
Sep 2 - Sep 3
Total with taxes and fees
7.2/10 Good! (2,292 reviews)
"This property is an excellent value, and has great proximity to the Art Institute of Chicago, and the Field Museum and the Museum Concourse. It is also well situated for public transportation, and is in a very safe and walkable part of downtown. It is also very close to Buckingham Fountain and Millennium ..."
Reviewed on Aug 21, 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 acclaimed art scene 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 entertainment choices.
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.
Things to do
Chicago's Dark Side Self-Guided Smartphone Walking Tour
$10
per adult
98% of travellers recommend
Chicago: Ghost Bus Tour of Haunted Locations
$54
per adult
100% of travellers recommend
Chicago's Ultimate City Bike Tour
$60
per adult
100% of travellers recommend
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.