The Loop Vacations from ￥278,193

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The Latest The Loop Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
Sep 9 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9/10 Wonderful! (652 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on Jul 27, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 9 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
Great stay :) Mr 47 didn’t disappoint

Reviewed on Aug 1, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 9 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on Jul 26, 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
Sep 9 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (3,342 reviews)
Property is loud. I wouldn't say five star. Rooms are narrow and relatively cramped.

Reviewed on Aug 2, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 9 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (2,253 reviews)
I loved how smooth the check in process was and all the amenities. Great rooms.

Reviewed on Aug 1, 2025

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 showing 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

The Loop Hotel Deals

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 ￥19,788 per night from Sep 1 to Sep 2
￥19,788
￥23,228 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (8,938 reviews)
"Very convenient location. Easy check-in, even with a very crowded lobby. Polite staff."

Reviewed on Aug 1, 2025

Congress Plaza Hotel
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥23,052 per night from Aug 26 to Aug 27
￥23,052
￥27,062 total
Aug 26 - Aug 27
includes taxes & fees
9.2/10 Wonderful! (3,486 reviews)
"Would be back soon !"

Reviewed on Jul 30, 2025

citizenM Chicago Downtown
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥30,954 per night from Sep 1 to Sep 2
￥30,954
￥40,664 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (3,323 reviews)
"Hotel staff, from reception desk, to housekeeping, wait staff, to door staff were superb: helpful and very responsive throughout my stay."

Reviewed on Aug 1, 2025

Hyatt Regency Chicago
See all 1,358 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 vacation package cost?
Much less than you might think — from as low as ￥278,193, 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.

Discover the most popular places to visit in The Loop

Millennium Park featuring a city, modern architecture and fall colors

Millennium Park

4.5/5(7,198 reviews)

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

Millennium Park
Chicago Riverwalk which includes a city, a bay or harbor and a river or creek

Chicago Riverwalk

4.5/5(1,535 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.

Chicago Riverwalk
Willis Tower which includes views, a city and a skyscraper

Willis Tower

4.5/5(3,369 reviews)

Visit the Skydeck and gaze down over the Chicago cityscape from a dazzling 1,353 feet above the sidewalk.

Willis Tower

Things to do

See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

￥6,597
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

￥6,157
per adult
86% of travellers recommend
Chicago: Architecture Boat Tour with Drinks
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,600
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.