The Loop Trip

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • Better together

    Save up to ₹43,962 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
Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was ₹88,737, price is now ₹64,409 per person
₹64,409
per person
21 Dec - 27 Dec
found 1 day ago
Return flight included
Houston (IAH) to Chicago (ORD)
9.2/10 Wonderful! (1,826 reviews)
excellent hotel, the staff, access to the city. We had a nice time in Chicago

Reviewed on 17 Oct 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ₹204,008, price is now ₹127,335 per person
₹127,335
per person
21 Dec - 27 Dec
found 1 day ago
Return flight included
Houston (IAH) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Excellent luxury atmosphere with second to none customer service. The bathroom was very nice. Although the toilet has a slight odor that was unexpected for the high quality room and hotel.

Reviewed on 15 Oct 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ₹98,918, price is now ₹66,170 per person
₹66,170
per person
21 Dec - 27 Dec
found 1 day ago
Return flight included
Houston (IAH) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Staff was amazing very help

Reviewed on 17 Oct 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was ₹112,515, price is now ₹75,290 per person
₹75,290
per person
21 Dec - 27 Dec
found 1 day ago
Return flight included
Houston (IAH) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.

Reviewed on 16 Oct 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was ₹103,409, price is now ₹75,617 per person
₹75,617
per person
21 Dec - 27 Dec
found 1 day ago
Return flight included
Houston (IAH) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine

Reviewed on 4 Oct 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 featuring 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 ₹11,204 per night from 2 Nov to 3 Nov
₹11,204
₹13,153 total
2 Nov - 3 Nov
includes taxes & fees
7.8/10 Good! (9,442 reviews)
Pleasant Stay for business
"Great location for downtown walking. The bar staff was friendly. I was here on business. The desk area didn't have any electrical outlets nearby for working but I get this isn't strictly a business hotel. If I was on vacation in CHI, this place would be ideal. Great value and the location was perfect. ..."

Reviewed on 16 Oct 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 ₹10,767 per night from 19 Oct to 20 Oct
₹10,767
₹12,640 total
19 Oct - 20 Oct
includes taxes & fees
9.2/10 Wonderful! (3,955 reviews)
"Staff was amazing"

Reviewed on 16 Oct 2025

citizenM Chicago Downtown
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₹18,619 per night from 24 Oct to 25 Oct
₹18,619
₹24,667 total
24 Oct - 25 Oct
includes taxes & fees
8.8/10 Excellent! (2,125 reviews)
"great!"

Reviewed on 11 Oct 2025

The Allegro Royal Sonesta Hotel Chicago Loop
See all 1,208 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 ₹64,409, 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 which includes autumn colours, modern architecture and street scenes

Millennium Park

4.5/5(147 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

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

Chicago Riverwalk

4.5/5(29 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
Art Institute of Chicago which includes art and interior views

Art Institute of Chicago

4.5/5(66 reviews)

From ancient masterpieces to eclectic modern art, uncover a treasure trove of works from all over the world and throughout history.

Art Institute of Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.