The Loop Holidays

Book a Hotel + Flight or Car together to unlock savings

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
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

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

Magnificent Mile

Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.

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

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

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

Lincoln Park

Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.

A nighttime cityscape with fireworks over a body of water, a Ferris wheel, and illuminated buildings.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).

Top hotels in The Loop

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
3.000.024 ₫
3.566.726 ₫ total
8 Sept - 9 Sept
includes taxes & fees
Congress Plaza Hotel
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
4.281.341 ₫
5.090.085 ₫ total
31 Aug - 1 Sept
includes taxes & fees
River Hotel
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

171 W Randolph St Chicago IL
Fully refundableReserve now, pay when you stay
5.105.634 ₫
6.830.561 ₫ total
30 Aug - 31 Aug
includes taxes & fees
9/10 Wonderful! (2,773 reviews)
"Easy and quick check in, staff were great"

Reviewed on 17 Aug 2026

The Allegro Royal Sonesta Hotel Chicago Loop
See all 1,210 properties in The 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.

Frequently asked questions

How much does a The Loop holiday package cost?
Much less than you might think — from as low as , in fact! By bundling flights, hotels and car rentals into your own custom-made package, your The Loop escape is only clicks away.
How do I get a cheap travel package to The Loop?
Booking a hotel and flight together with Expedia won't just save valuable time — it'll save you cash too. A The Loop holiday package makes it easy to organise the perfect trip. With more than 550 airlines all over the world to select from, finding convenient flights that fit your schedule will be no sweat. Not only that, we have over 1null000null000 properties globally to select from. Now that's what you call choice. Whatever your budget, Expedia will help show you the world.
Where should I stay in The Loop?
A journey to The Loop isn't over until you've seen McCormick Place and Millennium Park. Look for somewhere to stay within walking distance so you can easily access these impressive tourist attractions.
What are the top hotels in The Loop?
If it's your first time staying in The Loop, make a reservation at Canopy by Hilton Chicago Central Loop or Hilton Garden Inn Chicago Central Loop. Both hotels offer comfy beds and are favourites with many travellers.
How far in advance should I book my The Loop holiday?
To bag rock-bottom prices, book nice and early. Airlines typically advertise flights, along with some of the lowest fares, nearly a year prior to departure. Hotels, car rental and experiences should also be booked well in advance to avoid disappointment. If you were hoping for a last-minute getaway to The Loop, there are always plenty of great deals on Expedia. Check them out now!
What does an Expedia The Loop travel package include?
That depends on what you want. If you're travelling solo, you might decide to bundle flights and hotels. Taking the whole family to The Loop? A travel package including flights, hotels and rental cars might suit you better. Expedia gives you the freedom to customize your travel package.
Can I choose my airline with a The Loop Expedia holiday package?
Most definitely. Expedia has over 550 partner airlines to choose from globally. With so many choices, finding the ideal carrier to whisk you away to The Loop will be a snap.
If I'm not able to travel, can I cancel my The Loop holiday package?
We totally understand that life sometimes gets in the way of your plans. If you've booked a The Loop holiday package and need to cancel or change it, we're here to help. We recommend browsing our Customer Service Portal first for information. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel and rebook for free. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.

Stay near popular The Loop attractions

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

Chicago Riverwalk

9.6/10 (13,574 reviews)
After visiting Chicago Riverwalk, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront in this vibrant area or visit its top-notch restaurants.
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A cityscape with modern skyscrapers and the Cloud Gate sculpture.

Millennium Park

9.4/10 (30,446 reviews)
After visiting Millennium Park, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.
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A city skyline with tall skyscrapers, a river, and a bridge.

Willis Tower

9.0/10 (9,893 reviews)
Willis Tower is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the acclaimed theatre scene and fascinating museums in this vibrant area.
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A grand staircase in a historic building with classical architecture, including columns and ornate railings.

Art Institute of Chicago

9.4/10 (7,898 reviews)
You can spend an afternoon browsing the exhibits at Art Institute of Chicago in Chicago. Experience the fascinating museums and acclaimed theatre scene in this vibrant area.
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A large illuminated sign with the letters "CHICA" and a circular design.
Photo by © Choose Chicago

Chicago Theatre

9.0/10 (1,866 reviews)
You can make plans for a show at Chicago Theatre on your trip to Chicago. Amble around this vibrant area's riverfront or experience its entertainment choices.
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A cityscape with a prominent modern sculpture in the foreground and a mix of historic and contemporary buildings in the background.

Cloud Gate

9.4/10 (104 reviews)
You can learn about the history of Chicago with a visit to Cloud Gate. Discover the entertainment choices and notable monuments in this vibrant area.
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A city skyline with illuminated skyscrapers and a fountain with water jets.

Buckingham Fountain

9.2/10 (1,301 reviews)
Buckingham Fountain is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.
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A grand hall with a large, ornate dome ceiling and intricate wall decorations.

Chicago Cultural Center

9.2/10 (220 reviews)
Enjoy a stop at Chicago Cultural Center, an entertaining place to visit in Chicago. Discover the fascinating museums and notable monuments in this vibrant area.
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