South Loop Vacations from $377
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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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$377
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (3,105 reviews)
The staff was extremely accommodating, it was marathon week so I understand things can be tough, my issues were with the room as a whole. The shower would leak into the bathroom and completely cover the floor and when I informed staff I was having flooding problems they said oh it’s the shower curtain as if it’s a common issue. The wall paper in the bathroom was peeling off the wall. Tv guide didn’t work so you get to play channel roulette. On the plus side staff was great and they provided cold drinks in the morning, ac works really well
Reviewed on Oct 14, 2026
Villa Christina
Greater Grand Crossing
$617
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
10/10 Exceptional! (1 review)
Property was maintained very well, very clean with some artful style. Staff reaponsed quickly fie any needs or inquiry. Feels like a home. Community is safe and neighbors are nice. Street parking is reletively easy.
Reviewed on Aug 4, 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
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.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
South Loop Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$106 nightly
$126 total
Nov 11 - Nov 12
Total with taxes and fees
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$193 nightly
$227 total
Oct 30 - Oct 31
Total with taxes and fees
8.6/10 Excellent! (3,423 reviews)
"The property was great"
Reviewed on Oct 15, 2026
Travelodge by Wyndham Downtown Chicago
65 E Harrison St Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
$136 total
Nov 10 - Nov 11
Total with taxes and fees
7.8/10 Good! (2,906 reviews)
"The staff was so nice. The room was exactly what we needed. Excellent location, fine facilities. Thank you for the great place to stay."
Reviewed on Oct 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.
Stay near popular South Loop attractions
McCormick Place
8.8/10 (9,822 reviews)
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
Photo by © City of Chicago
Soldier Field
8.8/10 (7,063 reviews)
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Photo by City Of Chicago
Field Museum of Natural History
9.4/10 (1,744 reviews)
Dinosaur bones, rare gems and real Egyptian mummies are among the displays at this family favorite.
Adler Planetarium and Astronomy Museum
8.8/10 (248 reviews)
Opportunities for fun, learning and wonder abound at this historic and state-of-the-art museum on the pretty shore of Lake Michigan.
Northerly Island Natural Area
8.6/10 (28 reviews)
Bird life, paved paths and a built-in music venue give one of Chicago’s newest green spaces much to offer to nature lovers, exercisers and music fans.
Wintrust Arena
8.0/10 (70 reviews)
Catch an event at Wintrust Arena during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.
Columbia College Chicago
8.4/10 (164 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
8.8/10 (15 reviews)
You can learn about the history of Chicago with a visit to Dearborn Station. Experience the fascinating museums and acclaimed art scene in this vibrant area.
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
$158
per adult
80% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.