The Loop Holidays

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    Save up to €185 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
per person
24 Mar - 30 Mar
found 1 day ago
Return direct flight included
Larnaca (LCA) to Chicago (ORD)
8.4/10 Very Good! (1,617 reviews)
Beautiful room with an exceptional view of Lake Michigan!

Reviewed on 26 Jan 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
24 Mar - 30 Mar
found 1 day ago
Return direct flight included
Larnaca (LCA) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Nini was amazing! Her service was exceptional. The housekeeper on our floor greeted us every chance she got. From service to amenities and great location, I won’t be staying anywhere else next time I’m in Chicago.

Reviewed on 27 Jan 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
24 Mar - 30 Mar
found 1 day ago
Return direct flight included
Larnaca (LCA) to Chicago (ORD)
9/10 Wonderful! (282 reviews)
Amazing stay ! Love this property every time I’m in Chicago.

Reviewed on 20 Jan 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
24 Mar - 30 Mar
found 1 day ago
Return direct flight included
Larnaca (LCA) to Chicago (ORD)
9/10 Wonderful! (979 reviews)
the beds were extremely hard and uncomfortable. As well as the bedding. Did not feel it was worth the value for what I paid.

Reviewed on 28 Jan 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
24 Mar - 30 Mar
found 1 day ago
Return direct flight included
Larnaca (LCA) to Chicago (ORD)
9.4/10 Exceptional! (3,583 reviews)
We celebrated my birthday and were upgraded to a city and river view room. Absolutely loved the hotel.

Reviewed on 26 Jan 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

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Millennium Park are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

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 €104 per night from 1 Feb to 2 Feb
€104
includes taxes & fees
1 Feb - 2 Feb
7.8/10 Good! (8,428 reviews)
Excellent stay, great rates
"Wonderful, friendly staff. Our room amd view were amazing. Great prices, too!"

Reviewed on 26 Jan 2025

Congress Plaza Hotel
L7 Chicago by LOTTE
L7 Chicago by LOTTE
4.5 out of 5
225 N Wabash Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €200 per night from 9 Feb to 10 Feb
€200
includes taxes & fees
9 Feb - 10 Feb
9.6/10 Exceptional! (1,524 reviews)
"loved the view from river view suite"

Reviewed on 25 Jan 2025

L7 Chicago by LOTTE
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 €111 per night from 5 Feb to 6 Feb
€111
includes taxes & fees
5 Feb - 6 Feb
9.2/10 Wonderful! (2,607 reviews)
"Everything is great except the room is quite small. The lotion in the room seems to have been there for a long time. I pumped out a little, and it has already separated into oil and water—it's quite alarming."

Reviewed on 27 Jan 2025

citizenM Chicago Downtown
See all 1,295 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 €861, 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 featuring street scenes, autumn leaves and modern architecture

Millennium Park

4.5/5(147 reviews)

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

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

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)

Explore a massive collection of works celebrating different cultures and historical times, from ancient Egypt to modern installations.

Art Institute of Chicago

Things to do

Color Factory Chicago Ticket

Color Factory Chicago Ticket

€33
per adult
Color Factory Chicago Ticket
Chicago: Field Museum of Natural History Ticket or VIP Tour

Chicago: Field Museum of Natural History Ticket or VIP Tour

€28
per adult
86% of travellers recommend
Chicago: Field Museum of Natural History Ticket or VIP Tour
Private Chicago Scavenger Hunt: Eastside Art Heist

Eastside Chicago The Heist Exploration Game and Tour

€10
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.