The Loop Holidays

  • Plan, book, travel with confidence

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    Better together

    Save up to €185 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    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
Downtown Chicago which includes a city

Downtown Chicago

5 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.

Find hotels in Downtown Chicago

Top hotels in The Loop

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €177 per night from 4 Aug to 5 Aug
€177
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (8,976 reviews)
"The historic hotel was unique and had a beautiful lobby. The location was walkable to the bean and several food options. The downfall is that there is no parking onsite, and the parking nearby was $58 for 24 hours."

Reviewed on 25 Jul 2025

Congress Plaza Hotel
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
The price is €156 per night from 26 Aug to 27 Aug
€156
26 Aug - 27 Aug
includes taxes & fees
9.2/10 Wonderful! (3,438 reviews)
Fantastic find in Chicago
"What a great hotel -selected from many close to my conference at the Hyatt. It was also walking distance (1.2 miles) from Union Station (Amtrak). Hotel check-in and check-out is seamless -all done at central kiosk. Hotel staff ever-present to assist. Rooms are exceptionally clean and comfortable. ..."

Reviewed on 24 Jul 2025

citizenM Chicago Downtown
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
323 E Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €185 per night from 10 Aug to 11 Aug
€185
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (2,509 reviews)
"Best location to stay"

Reviewed on 26 Jul 2025

Swissotel - Chicago
See all 1,280 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.

Popular places to visit

Millennium Park featuring street scenes, autumn leaves and modern architecture

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Chicago Riverwalk featuring a bay or harbour, a city and a river or creek

Chicago Riverwalk

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.

Chicago Riverwalk
Art Institute of Chicago which includes art and interior views

Art Institute of Chicago

Explore a massive collection of works celebrating different cultures and historical times, from ancient Egypt to modern installations.

Art Institute of Chicago

Things to do

See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

€39
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

€36
per adult
88% of travellers recommend
Chicago: Architecture Boat Tour with Drinks
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

€21
per adult
86% of travellers recommend
Chicago: 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.