A cityscape with tall buildings, including a prominent skyscraper with a spire.

South Loop Vacation Packages

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    • The Latest South Loop Vacation Packages

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    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 cityscape with tall skyscrapers and a historic tower.

    The Chicago Theatre with ornate architecture and a prominent marquee.

    A river with boats, surrounded by tall buildings and a clear sky.

    The Chicago Theatre with marquee lights and a large illuminated sign.

    A cityscape with a mix of modern skyscrapers and a historic tower.

    View properties in map for Downtown Chicago

    Downtown Chicago

    The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

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    A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.

    Photo by © City of Chicago

    A city intersection with tall buildings, including a historic building labeled "Water Tower Place."

    A cityscape with tall buildings, including a historic tower and modern skyscrapers.

    Photo by TM

    A cityscape with tall buildings, a prominent clock tower, and a busy intersection with moving vehicles.

    A nighttime cityscape with illuminated skyscrapers and a prominent clock tower.

    View properties in map for Magnificent Mile

    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.

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

    A nighttime cityscape with illuminated buildings and a bridge over a river.

    A nighttime cityscape with illuminated skyscrapers and a river.

    A river with a bridge, modern buildings, and a historic tower.

    A river with a yellow boat and a white yacht. In the background, there are tall buildings and a bridge.

    View properties in map for The Loop

    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.

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    A large, historic building with a central tower and multiple windows, located near a body of water.

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

    A nighttime cityscape with illuminated buildings, a river, and a bridge.

    Photo by Katie Robinson

    A modern building with illuminated signage, surrounded by urban skyscrapers and a curved road with light trails.

    Photo by LJ Alan

    A coastal cityscape with a long beach, dense urban buildings, and a clear blue sea.

    Photo by Robert Bartolino

    View properties in map for River North

    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.

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    A river with a city skyline in the background, surrounded by green trees and grass.

    A city skyline with a river, green spaces, and a baseball field.

    A city skyline with tall buildings, a frozen lake, and leafless trees in a park.

    A city skyline with high-rise buildings, a calm river reflecting the structures, and a park with trees and a walking path.

    A city skyline with a park and a lake.

    View properties in map for Lincoln Park

    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.

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    Discover the most popular places to visit in South Loop

    A modern glass building with a curved roof, surrounded by a landscaped garden and a water feature.

    McCormick Place

    Rating: 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 stadium surrounded by a cityscape with modern buildings.

    Photo by © City of Chicago

    Soldier Field

    Rating: 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 coastal cityscape with a prominent skyscraper, a waterfront promenade, and a large Ferris wheel.

    Wintrust Arena

    Rating: 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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    The Field Museum building with large banners and classical columns.

    Photo by City Of Chicago

    Field Museum of Natural History

    Rating: 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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    An aerial view of a circular plaza with a central monument, surrounding pathways, and a waterfront.

    Adler Planetarium and Astronomy Museum

    Rating: 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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    Arie Crown Theater

    Rating: 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 art scene in this vibrant area.

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    Columbia College Chicago

    Rating: 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.

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    Dearborn Station

    Rating: 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.

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    What to do near South Loop

    360 CHICAGO Observation Deck (Hancock Center)

    360 CHICAGO Observation Deck

    CA $34

    per adult

    86% of travellers recommend

    Skydeck Chicago at Willis Tower

    Skydeck Chicago at Willis Tower

    CA $60

    per adult

    84% of travellers recommend

    See Chicago's magnificent skyline at night!

    Chicago By Night River and Lake Cruise

    CA $71

    per adult

    92% of travellers recommend

    See all activities near South Loop

    South Loop Hotel Deals

    Hilton Vacation Club Hotel Blake Chicago

    A hotel entrance with a marquee sign, a blue carpet, and a flag.
    • Address: 500 South Dearborn Street, Chicago, IL, 60605, US
    • Location: South Loop
    • Star rating: 4/5
    • Guest rating: 9.6/10 (Exceptional, 1210 reviews)
    • Price: CA $159, CA $189 total, includes taxes & fees, Dec 10 - Dec 11

    Best Western Grant Park Hotel

    A hotel room with a large bed, a desk with a flat-screen TV, a chair, and a window with curtains.
    • Address: 1100 S Michigan Ave, Chicago, IL, 60605, US
    • Location: South Loop
    • Star rating: 2.5/5
    • Guest rating: 8.2/10 (Very good, 2751 reviews)
    • Price: CA $122, CA $145 total, includes taxes & fees, Dec 7 - Dec 8
    • Review: Nice location. Restaurants are just walking distance.

    Hilton Garden Inn Chicago Downtown South Loop

    A hot tub with a metal ladder, surrounded by white tiled walls and floor, with a large window providing a view of the cityscape.
    • Address: 55 E 11th Street, Chicago, IL, 60605, US
    • Location: South Loop
    • Star rating: 3/5
    • Guest rating: 8.8/10 (Excellent, 2206 reviews)
    • Price: CA $138, CA $162 total, includes taxes & fees, Nov 23 - Nov 24
    • Review: The room was not as clean, the staff was very RUDE, The front desk manager Dalisa had an attitude and she is racist.

    Hampton Inn Chicago McCormick Place

    A hotel room with two beds, a desk, a TV, and a lamp.
    • Address: 123 East Cermak, Suite 100, Chicago, IL, 60616, US
    • Location: South Loop
    • Star rating: 3/5
    • Guest rating: 9/10 (Wonderful, 1046 reviews)
    • Price: CA $124, CA $147 total, includes taxes & fees, Dec 14 - Dec 15
    • Review: breakfast

    Hilton Chicago

    A multi-story building with a prominent entrance featuring a large archway and a sign.
    • Address: 720 S Michigan Ave, Chicago, IL, 60605, US
    • Location: South Loop
    • Star rating: 4/5
    • Guest rating: 8.6/10 (Excellent, 3543 reviews)
    • Price: CA $193, CA $271 total, includes taxes & fees, Nov 22 - Nov 23

    Home2 Suites by Hilton Chicago McCormick Place

    A modern living room with a fireplace, two red sofas, a green armchair, and a coffee table.
    • Address: 123 E. CERMAK ROAD, Chicago, IL, 60616, US
    • Location: South Loop
    • Star rating: 3/5
    • Guest rating: 9.2/10 (Wonderful, 958 reviews)
    • Price: CA $116, CA $136 total, includes taxes & fees, Dec 14 - Dec 15

    Le Méridien Essex Chicago

    A modern living room with a sofa, armchairs, and a coffee table. There are bookshelves and a decorative wall panel.
    • Address: 800 S Michigan Ave, Chicago, IL, 60605, US
    • Location: South Loop
    • Star rating: 4/5
    • Guest rating: 9/10 (Wonderful, 1002 reviews)
    • Price: CA $160, CA $215 total, includes taxes & fees, Dec 7 - Dec 8
    • Review: "Wonderful staff!! Welcoming, friendly, and very helpful. We ended up arriving 2 hours before check-in, but staff had no problem helping us out and letting us get our room early. Valet staff hepful when we needed to get an item from the car, James was so awesome helping with luggage and to our room. Housekeeping checked in to see if we were happy with the room, which was very clean!! Each contact we had with staff was a positive one. Lobby was small but cute and eclectic. Wish there was a...

    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.

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    Frequently Asked Questions

    How much does a South Loop vacation package cost?

    Starting from a low CA $1,127, a vacation package is your passport to low-cost travel. Custom make your South Loop escape by selecting from our extensive range of hotels, flights and rental cars.

    How do I get a cheap travel package to South Loop?

    Creating your own South Loop vacation package with Expedia is a simple way to save. We have more than 550 airlines and 1,000,000 properties spread across the globe. With such a wonderful range to pick from, you'll have no trouble creating your next dream getaway.

    Where should I stay in South Loop?

    Make sightseeing a breeze by staying someplace close to South Loop's iconic attractions. McCormick Place and Millennium Park are two of the best in the area.

    What are the top hotels in South Loop?

    Sonder South Wabash and Hotel BnB are a couple of the most sought-after properties in South Loop. Why not take a look at the rates and facilities at each and then decide?

    How far in advance should I book my South Loop vacation?

    It can be tricky to know when the best time is to book your trip to South Loop. But generally the earlier you book, the more affordable the prices. In some cases, you can book your flights and hotels up to 12 months before departure. If you're hoping for a last-minute getaway, no need to worry! There are fantastic deals posted on Expedia all the time.

    What does an Expedia South Loop travel package include?

    That depends on what type of getaway you're thinking about. South Loop vacation deals can include hotels, car rentals and flights. You can mix and match to create the package that fits your needs. You can also add on experiences and activities after you've booked to score even bigger discounts.

    What should I know before booking a South Loop travel package?

    So many places to wander around, so many things to see and do. With a package, you can check more of them off your list. Combine your hotels, flights and rental cars and see how much you save.

    Can I choose my airline with a South Loop Expedia vacation package?

    You sure can. Expedia has access to more than 550 partner airlines worldwide, so choose the carrier that's a good fit for your needs.

    If I'm not able to travel, can I cancel my South Loop vacation package?

    Yes, you can cancel your South Loop booking if your travel plans have been upended. Whether you'll incur a penalty or not depends on your hotel, airline or car rental company. You may be able to change or cancel for free if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.

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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.