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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was ₹99,785, price is now ₹55,895 per person
₹55,895
per person
5 May - 8 May
found 1 day ago
Return direct flight included
Asheville (AVL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great location, clean, friendly staff, courier free

Reviewed on 25 Feb 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ₹100,592, price is now ₹72,806 per person
₹72,806
per person
5 May - 8 May
found 1 day ago
Return direct flight included
Asheville (AVL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Had a great stay!! Kelly at the front desk was so sweet

Reviewed on 22 Feb 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ₹102,864, price is now ₹74,814 per person
₹74,814
per person
5 May - 8 May
found 1 day ago
Return direct flight included
Asheville (AVL) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
From beginning to the end my stay was a 10/10. I only stayed one night but that one night was worth it.

Reviewed on 24 Feb 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ₹139,032, price is now ₹103,062 per person
₹103,062
per person
5 May - 8 May
found 1 day ago
Return direct flight included
Asheville (AVL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
We had a great stay!

Reviewed on 23 Feb 2026

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was ₹89,528, price is now ₹66,976 per person
₹66,976
per person
5 May - 8 May
found 1 day ago
Return direct flight included
Asheville (AVL) to Chicago (ORD)
9.2/10 Wonderful! (1,862 reviews)
Everything was great, I really enjoyed my stay!

Reviewed on 25 Feb 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 featuring a city

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.

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 ₹24,466 per night from 13 Mar to 14 Mar
₹24,466
₹28,720 total
13 Mar - 14 Mar
includes taxes & fees
8/10 Very Good! (9,934 reviews)
The room was spotless, security was a great help with everything.

Reviewed on 25 Feb 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₹12,604 per night from 5 Mar to 6 Mar
₹12,604
₹17,465 total
5 Mar - 6 Mar
includes taxes & fees
8.6/10 Excellent! (2,651 reviews)
Staff was great and room was clean

Reviewed on 24 Feb 2026

Hilton Chicago
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 ₹17,099 per night from 25 Mar to 26 Mar
₹17,099
₹22,742 total
25 Mar - 26 Mar
includes taxes & fees
9.4/10 Exceptional! (3,492 reviews)
The room was spotless. The front desk helped make sure my reservation was taken care of despite travel delays outside of my control. Highly recommended this property and their staff

Reviewed on 24 Feb 2026

Hyatt Regency Chicago
See all 1,233 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 ₹55,895, 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
Willis Tower featuring city views, mist or fog and a city

Willis Tower

4.5/5(81 reviews)

The Skydeck at Willis Tower offers the best place in Chicago for a bird’s eye view across the breadth of the city and Lake Michigan.

Willis Tower

Explore a world of travel with Expedia

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