The Loop Holidays

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    Save up to €185 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €863, price is now €577 per person
€577
per person
26 Oct - 29 Oct
found 6 hours ago
Return direct flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,070 reviews)
This is an exceptional hotel. The rooms are clean. The service is impeccable, and the products!! The signature scent is to die for. It is now a part of my life. I had to buy a candle on the way out and have already visited the online store for body wash and lotion. Well done. There are a lot of choices in Chicago, but this is now my go to. Will definitely be back!

Reviewed on 12 Sept 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €1,956, price is now €1,213 per person
€1,213
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
The hotel needs a facelift in its rooms. It’s a 5-star hotel, and you expect more. The restaurant was good, and the food was good. On our second day, my server told me a croissant came with my breakfast, but I got charged. I didn’t say anything. On the 20th floor, you can hear everything from outside, like you are on the second floor. No soundproofing? It's hard to sleep at night.

Reviewed on 17 Sept 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was €2,153, price is now €1,376 per person
€1,376
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
Got pick pocketed in the elevator. I really like this hotel. Plan to return.

Reviewed on 8 Sept 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €1,450, price is now €941 per person
€941
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,195 reviews)
Nice area, easy to get to, close to things to do

Reviewed on 18 Sept 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was €1,192, price is now €800 per person
€800
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,014 reviews)
Convenient location for what we were doing. Highly suggested if you are going to a show at the Chicago Theater.

Reviewed on 17 Sept 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 which includes 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
7.8/10 Good! (9,188 reviews)
"Clean room, Confortable bed"

Reviewed on 16 Sept 2025

Get rates
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 €155 per night from 22 Sept to 23 Sept
€155
22 Sept - 23 Sept
includes taxes & fees
9.2/10 Wonderful! (3,799 reviews)
"Love how close you are to everything when staying here. Staff was also amazing!!"

Reviewed on 16 Sept 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 €291 per night from 2 Oct to 3 Oct
€291
2 Oct - 3 Oct
includes taxes & fees
9.2/10 Wonderful! (3,349 reviews)
"Airr"

Reviewed on 16 Sept 2025

Hyatt Regency Chicago
See all 1,239 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 €577, 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

See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

€39
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

€21
per adult
86% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

€36
per adult
88% of travellers recommend
Chicago: Architecture Boat Tour with Drinks
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.