South Loop Vacations from $628

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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

Hotel Felix River North/Magnificent Mile

Downtown Chicago
Save 100% on your flight
$628
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,960 reviews)
The staff was easily the best part of my stay at Hotel Felix. Everyone I interacted with was incredibly kind, accommodating, and helpful. The staff who assisted me with check-in and anything else I needed during my stay were wonderful, housekeeping was great, and overall the customer service was consistently warm and pleasant. I also appreciated that the hotel had breakfast available for purchase on-site, along with complimentary coffee and water throughout the day. The lobby is very nice and gives the hotel a polished first impression. Unfortunately, that did not really translate to the room. My room was extremely small and felt more like a shoebox with a bathroom attached. There was no closet, no refrigerator, and very little space overall. The robe folded in the bathroom had a visible stain on the collar, and there were stains on the ceiling as well. The biggest issue for me was the noise. I could hear people opening, closing, locking, and slamming doors throughout the hallway very clearly. On multiple nights it actually woke me out of my sleep because the sound was so close and abrupt that it made me think someone was trying to enter my room. I’m not sure whether that comes down to thin walls, limited soundproofing, or the way the doors are designed, but it was definitely disruptive. Overall, the hotel did what I needed it to do: it gave me somewhere to put my things and sleep at night. If you’re traveling and just need a very basic place to stay, it gets the job d

Reviewed on Aug 30, 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
Save 100% on your flight
$1,197
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
It was a great stay and it was a great location for all my sightseeing

Reviewed on Aug 30, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
Save 100% on your flight
$811
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (159 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
Save 100% on your flight
$1,119
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,654 reviews)
Parking wasn't free as advertised

Reviewed on Aug 30, 2026

Kinzie Hotel

Kinzie Hotel

Downtown Chicago
Save 100% on your flight
$786
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (2,218 reviews)
Good location. Clean.

Reviewed on Aug 30, 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
A busy city street with tall buildings, a bus, and cars.

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.

A river with yellow boats, a bridge, and tall buildings.

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.

A neon sign reading "Blue Chicago on Clark" in an ornate archway.

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.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

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.

A wooden pavilion with a view of a city skyline and a body of water.

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

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$109 nightly
$130 total
Sep 8 - Sep 9
Total with taxes and fees
8/10 Very Good! (10,231 reviews)
"I had a good experience, no complaints at all"

Reviewed on Aug 30, 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$194 nightly
$230 total
Sep 7 - Sep 8
Total with taxes and fees
Hilton Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL
Fully refundableReserve now, pay when you stay
$94 nightly
$112 total
Aug 31 - Sep 1
Total with taxes and fees
Travelodge by Wyndham Downtown Chicago
See all 4,496 properties in South Loop
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

A large stadium surrounded by a cityscape with modern buildings.
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.
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A modern cityscape with tall buildings, a clear sky, and a tree-lined street.
Photo by © Cesar Russ Photography

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.
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A large building with a dome and columns, surrounded by a well-maintained lawn and trees.
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.
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A modern building with a dome and a triangular glass facade.

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.
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A river with boats, a city skyline, and a park with a walking path.

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.
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A city skyline with high-rise buildings, a marina with boats, and a large body of water.

Northerly Island

Commune with nature and explore the great outdoors at Northerly Island during your travels in Chicago. Experience the acclaimed art scene and entertainment choices in this vibrant area.
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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.
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Arie Crown Theater

8.0/10 (9 reviews)
You can enjoy a show at Arie Crown Theater on your trip to Chicago. Experience the fascinating museums and acclaimed theater scene in this vibrant area.
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$27
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

$47
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Flyover in Chicago

Flyover in Chicago

$28
per adult
96% of travellers recommend
Flyover in Chicago
See all activities in Chicago

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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.