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

The Loop Vacations from $266

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Your The Loop Vacation

Experience the best that The Loop has to offer with a tailor-made The Loop vacation package. From its bars and pubs and history to its festivals, get ready to fall for the charms of this food-lovers neighborhood. Your trip to The Loop wouldn't be complete without seeing popular attractions nearby such as Millennium Park, Willis Tower and Art Institute of Chicago. Expedia can help you turn your ideal The Loop vacation into reality, no matter your budget or travel plans.

The Latest The Loop Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A grand lobby with a central bar, high ceilings, and classical architecture.
    Jan 7 - Jan 10

    THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,004 reviews)
    "We loved this hotel! The. Staff was super friendly and the hotel was very comfortable and beautiful. It felt like we were staying at the continental from the John Wick movies ❤️ the bathrooms had the perfect warm lightning....not that bright blue white light that blinds you. The staff were super nice. Always accommodating. Will definitely stay there again, next time we come to Chicago ❤️"
    Reviewed November 6, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $409
    $266
    per traveler
    found 1 day ago
    THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
  • A couple dining at a table with a view of a cityscape and a sunset.
    Dec 10 - Dec 13

    Park Hyatt Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,001 reviews)
    "Given the price point and other reviews, we came here expecting a luxury stay similar to the Waldorf Astoria, Four Seasons, and Peninsula, which are some of our favorite properties to stay at. However, everything from the service and cleanliness to the ambiance of the entrance and lobby and the amenities (other than the gym, which was excellent) is best described as an upgraded version of an average Hilton, Hyatt, or Marriott. For example, there was a hair in the bed. When we reported it, the..."
    Reviewed November 4, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - MDW • Nonstop ORD - ATL • Nonstop
    $1,826
    $1,237
    per traveler
    found 19 hours ago
    Park Hyatt Chicago
  • A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.
    Jan 7 - Jan 10

    Le Méridien Essex Chicago + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.0/10 - Wonderful (1,000 reviews)
    "I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything."
    Reviewed November 3, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $466
    $323
    per traveler
    found 1 day ago
    Le Méridien Essex Chicago
  • A street view with outdoor seating, a building with a sign, and tall skyscrapers in the background.
    Dec 7 - Dec 10

    The Talbott, Autograph Collection + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.4/10 - Exceptional (194 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $567
    $394
    per traveler
    found 1 day ago
    The Talbott, Autograph Collection
  • The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.
    Jan 7 - Jan 10

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (5,648 reviews)
    "The hotel was well maintained and the staff were friendly and professional. I would definitely stay there again."
    Reviewed November 6, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $478
    $333
    per traveler
    found 1 day ago
    Hotel Riu Plaza Chicago

Where to stay in The Loop

Find the best The Loop areas and neighborhoods for the activities you enjoy most. Learn more about The Loop
Learn more about The Loop
A cityscape with tall skyscrapers and a historic tower.

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.

A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.
Photo by © City of Chicago
Open Photo by © City of Chicago

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

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

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.

A cityscape with modern skyscrapers and a curved highway.

West Loop

Consider a visit to The Old Post Office and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center.

Discover the most popular places to visit in The Loop

A large metallic sphere sculpture in a public square surrounded by tall buildings.
Photo by TM
Open Photo by TM

Millennium Park

9.4/10 (30,446 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
See properties

What to do near The Loop

360 CHICAGO Observation Deck (Hancock Center)

360 CHICAGO Observation Deck

$24
per adult
86% of travelers recommend
360 CHICAGO Observation Deck
See all activities near The Loop

The Loop Hotel Deals

A modern urban building with a distinctive curved facade, a prominent '10pin' sign, and a 'Tertius' restaurant on the ground floor.

Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Chicago Downtown, Autograph Collection by Marriott
4.0 star property
River North, 0.3 mi from The Loop
9.2 out of 10, Wonderful, (1,000 reviews)
"Amazing location!! Clean good big rooms clean bathrooms and quiet. Thick walls!"
$102 nightly
The price is $122
Nov 22 - Nov 23
Total with taxes and fees
Hotel Chicago Downtown, Autograph Collection by Marriott
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.
See all properties in The Loop
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.