South Loop Vacations from $370
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was $639, price is now $370 per person
$370
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
Muy bien ubicado, puedes ir caminando por todo el loop y todo esta cerca (si va al downtown), el personal es amable, los cuartos amplios y bonitos, la vista muy bonita (solo que hay edificios al rededor y no ves mas). Los precios de todo en el hotel me parecen un poco elevados.
Reviewed on Apr 15, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $871, price is now $454 per person
$454
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
Nice hotel, lovely rooftop bar, good breakfast. Would definitely stay here again.
Reviewed on Apr 15, 2026
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,760, price is now $1,071 per person
$1,071
per person
Jul 5 - Jul 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,123 reviews)
The staff at the Pendry are top notch. We arrived early and just wanted to drop our bags off, but the staff was able to check us in several hours early. Upon learning it was my birthday, the bell hop brought me a glass of wine from the bar and later, the staff sent up a bottle of prosecco and birthday cupcakes. Our room
Reviewed on Apr 7, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,407, price is now $861 per person
$861
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,647 reviews)
I was pleasantly surprised that the photos matched what the room would look like and especially the view. Staff and the hospitality of the hotel was excellent and I definitely would select to stay here again.
Reviewed on Apr 15, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,668, price is now $1,023 per person
$1,023
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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! (10,151 reviews)
Room looked great, basically more like a studio than a hotel room.
Reviewed on Apr 15, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$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! (2,729 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! (1,942 reviews)
Very nice room, amenities are sparse. Had to ask for coffee and tea because they were not automatically replenished. Tried to use the indoor pool, but unfortunately it was monopolized by children and rude teenagers. Location downtown was very good and easy to use transit system both bus and ...
Reviewed on Apr 15, 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.
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.
Dearborn Station
4.5/5(13 reviews)
You can learn about the history of Chicago with a visit to Dearborn Station. Experience the acclaimed theater scene and entertainment choices in this vibrant area.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
98% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
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
- 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.