The Loop Vacations from ￥461,740
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest The Loop Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥461,740
per person
Nov 15 - Nov 20
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
Nice place and location, especially if you have a good room. It's expensive but you get good experiance
Reviewed on Aug 26, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
￥465,592
per person
Oct 7 - Oct 13
found 18 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9/10 Wonderful! (1,462 reviews)
The staff was so welcoming and updated our room to a better room. The weekend we stayed had lots of activities to do while we were here. I’d recommend planning your trip here
Reviewed on Aug 25, 2026
Swissotel - Chicago
Downtown Chicago
￥471,246
per person
Nov 15 - Nov 20
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
The views are nice. The room is more simple. The bathroom needs to be upgraded. Definitely just 3.5-4*. The late night snack area is a nice feature though.
Reviewed on Aug 25, 2026
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
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.
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.
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.
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.
Streeterville
Navy Pier and Michigan Avenue are just a few worthwhile attractions to visit in Streeterville. Travelers also love the fascinating museums, panoramic lake views, and popular shops.
The Loop Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
￥16,977
per night
Sep 8 - Sep 9
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
Fully refundableReserve now, pay when you stay
￥29,086
per night
Sep 7 - Sep 8
River Hotel
75 East Wacker Drive Chicago IL
￥22,777
per night
Sep 7 - Sep 8
8.8/10 Excellent! (5,453 reviews)
"Overall a great stay location is perfect and the view was amazing. Room was basic and simple but it was clean. Everything worked so I’d recommend it for future travelers."
Reviewed on Aug 26, 2026
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 vacation package cost?
Much less than you might think — from as low as ￥461,740, 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 vacation package makes it easy to organize 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 favorites with many travelers.
How far in advance should I book my The Loop vacation?
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 traveling 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 vacation 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 vacation package?
We totally understand that life sometimes gets in the way of your plans. If you've booked a The Loop vacation 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
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.
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.
Art Institute of Chicago
9.4/10 (7,898 reviews)
Explore a massive collection of works celebrating different cultures and historical times, from ancient Egypt to modern installations.
Willis Tower
9.0/10 (9,893 reviews)
Visit the Skydeck and gaze down over the Chicago cityscape from a dazzling 1,353 feet above the sidewalk.
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.
Cloud Gate
9.4/10 (104 reviews)
You can learn about the history of Chicago with a stop at Cloud Gate. Discover the entertainment choices and notable monuments in this vibrant area.
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.
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.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
￥3,920
per adult
90% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
￥7,518
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.