The Loop Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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

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

Magnificent Mile

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

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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.

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

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

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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).

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Top hotels in The Loop

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
S$154
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,293 reviews)
"Staffs are helpful."

Reviewed on 23 Aug, 2026

Congress Plaza 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
S$335
30 Aug - 31 Aug
includes taxes & fees
9/10 Wonderful! (2,819 reviews)
"Veryyyy small room and bathroom. No breakfast or dining room open for Sunday morning guests."

Reviewed on 23 Aug, 2026

The Allegro Royal Sonesta Hotel Chicago Loop
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
S$217
30 Aug - 31 Aug
includes taxes & fees
8.8/10 Excellent! (5,436 reviews)
"The view was beautiful. The hot water took a while to get hot but other than that I enjoyed my stay."

Reviewed on 23 Aug, 2026

River Hotel
See all 1,204 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 1,000,000 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)
Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.
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A cityscape with modern skyscrapers and the Cloud Gate sculpture.

Millennium Park

9.4/10 (30,446 reviews)
One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.
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A city skyline with tall skyscrapers, a river, and a bridge.

Willis Tower

9.0/10 (9,893 reviews)
The Skydeck at Willis Tower offers the best place in Chicago for a bird’s eye view across the breadth of the city and Lake Michigan.
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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)
From ancient masterpieces to eclectic modern art, uncover a treasure trove of works from all over the world and throughout history.
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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)
See a stage show at this iconic cultural beacon, which still captures all the splendor of a trip to the movie theater in the early 20th century.
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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)
This enormous art deco installation gives free regular water and light shows symbolizing the power and might of Lake Michigan.
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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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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

S$35
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

S$32
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago's Navy Pier Centennial Wheel Ticket

Chicago's Navy Pier Centennial Wheel Ticket

S$31
per adult
100% of travellers recommend
Chicago's Navy Pier Centennial Wheel Ticket
See all activities in Chicago

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.