The Loop Vacations from ￥337,270

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The Latest The Loop Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (1,610 reviews)
Beautiful place, great location, parking nearby.

Reviewed on Apr 29, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,546 reviews)
Excellent experience!

Reviewed on Apr 28, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,605 reviews)
TV did not work. Was told that it was a problem with the system for everyone and would be fixed in 10 minutes. An hour later I called again and was told the engineer would come to our room next. The engineer never came. No follow up from anyone else. The TV did not work until the next day.

Reviewed on Apr 29, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Gorgeous views, great in room dining, staff were very nice

Reviewed on Apr 28, 2025

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (1,444 reviews)
The hotel clerk who welcomed us upon checking in was the most gracious!

Reviewed on Apr 24, 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 ￥16,932 per night from May 27 to May 28
￥16,932
￥19,877 total
includes taxes & fees
May 27 - May 28
7.8/10 Good! (8,729 reviews)
"Loved our stay! Cool historic hotel in an excellent location. Breakfast buffet was $29.95 and had wonderful variety of choices."

Reviewed on Apr 28, 2025

Congress Plaza Hotel
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 ￥24,913 per night from May 2 to May 3
￥24,913
￥33,418 total
includes taxes & fees
May 2 - May 3
8.8/10 Excellent! (2,070 reviews)
"The location was a little confusing at first, but once we became more familiar with the area, it was pretty conveniently located, right on the water and close to many busses. The staff was helpful and attentive."

Reviewed on Apr 29, 2025

Swissotel - Chicago
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥16,922 per night from May 26 to May 27
￥16,922
￥19,865 total
includes taxes & fees
May 26 - May 27
8.6/10 Excellent! (4,095 reviews)
"Thus property was beautiful, very clean, friendly staff and there was free coffee. Amazing views made it even better. We walked across the street to the River Walk and down the block to a boat tour. We also walked to a bar and a restaurant downtown. If we go back to Chicago, we would definitely stay ..."

Reviewed on Apr 27, 2025

River Hotel
See all 1,164 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 ￥337,270, 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

Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

￥6,362
per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,104
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Private Chicago Scavenger Hunt: Eastside Art Heist

Eastside Chicago The Heist Exploration Game and Tour

￥1,555
per adult
Eastside Chicago The Heist Exploration Game and Tour
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.