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

The Loop Vacations from $286

Book a Hotel + Flight or Car together to unlock savings

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 couple sitting on a blue couch with a table in front of them, holding drinks and a pizza.
    Jan 29 - Feb 1

    Hotel Saint Clair- Magnificent Mile + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.6/10 - Excellent (2,409 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $406
    $286
    per traveler
    found 1 day ago
    Hotel Saint Clair- Magnificent Mile
  • An outdoor seating area with a fire pit, wooden benches, and tables, surrounded by large windows and string lights.
    Jan 23 - Jan 27

    The Emily Hotel + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,359 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $1,183
    $719
    per traveler
    found 21 hours ago
    The Emily Hotel
  • A modern living room with a grey sofa, a round coffee table with a plant, and a TV mounted on the wall.
    Jan 23 - Jan 27

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (609 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $948
    $622
    per traveler
    found 1 day ago
    Level Chicago Fulton Market
  • The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.
    Jan 29 - Feb 1

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (5,689 reviews)
    "朝食が頂ける事が素晴らしく思うと共にそのアイテムも多数あり満足でしたが、連泊しておりますと少しずつアレンジを加えて頂けますと飽きがこないと思います。"
    Reviewed November 12, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $474
    $322
    per traveler
    found 1 day ago
    Hotel Riu Plaza Chicago
  • A hotel room with a bed, a bedside table with a lamp, and a chair.
    Jan 29 - Feb 1

    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
    $422
    $289
    per traveler
    found 1 day ago
    Le Méridien Essex 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 hotel entrance with a prominent 'MORTON' sign, a 'HOTEL BLAKE CHICAGO' sign, and a '542' address number.

Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
The Loop
9.6 out of 10, Exceptional, (1,208 reviews)
$111 nightly
The price is $132
Dec 10 - Dec 11
Total with taxes and fees
Hilton Vacation Club Hotel Blake Chicago
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.