The Loop Holidays from AU$2,249

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Your The Loop Holiday

Experience the best that The Loop has to offer with a tailor-made The Loop holiday package. From its bars and pubs and history to its festivals, get ready to fall for the charms of this food-lovers neighbourhood. Your trip to The Loop wouldn't be complete without seeing popular attractions nearby such as Millennium Park, Willis Tower and Art Institute of Chicago. Expedia can help you turn your ideal The Loop holiday into reality, no matter your budget or travel plans.

Top Holiday Package Deals in The Loop

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
O'Hare
per person
16 Oct - 23 Oct
found 1 hour ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.8/10 Excellent! (2,250 reviews)
it was good as usual

Reviewed on 8 Aug. 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
per person
16 Oct - 23 Oct
found 1 hour ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.2/10 Very Good! (2,084 reviews)
I just needed a quiet clean room for the night. Grateful

Reviewed on 7 Aug. 2025

Sonesta Chicago O'Hare Airport Rosemont

Sonesta Chicago O'Hare Airport Rosemont

3 out of 5
O'Hare
per person
16 Oct - 23 Oct
found 1 hour ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.6/10 Excellent! (1,537 reviews)
Sonesta was lovely. Easy check in. Nice room. Pillows not so great. Shuttle service was excellent as was all the staff!

Reviewed on 8 Aug. 2025

DoubleTree by Hilton Chicago Schaumburg

DoubleTree by Hilton Chicago Schaumburg

4 out of 5
per person
16 Oct - 23 Oct
found 1 hour ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
7.4/10 Good! (1,009 reviews)
Very very quiet slept so good Needed pool and gym and cooking for myself

Reviewed on 7 Aug. 2025

Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
O'Hare
per person
16 Oct - 23 Oct
found 1 hour ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.8/10 Excellent! (1,001 reviews)
Clean and quiet. Great location and close to ORD

Reviewed on 6 Aug. 2025

Our guide on 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

Our pick of the best 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 AU$452 per night from 7 Sept to 8 Sept
AU$452
7 Sept - 8 Sept
includes taxes & fees
7.8/10 Good! (8,921 reviews)
"Took water awhile to get hot for shower, and parking is ridiculously expensive. Other than that enjoyed staying at hotel"

Reviewed on 8 Aug. 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$350 per night from 4 Sept to 5 Sept
AU$350
4 Sept - 5 Sept
includes taxes & fees
8.2/10 Very Good! (1,831 reviews)
"Great!"

Reviewed on 5 Aug. 2025

Palmer House a Hilton 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 AU$281 per night from 26 Aug to 27 Aug
AU$281
26 Aug - 27 Aug
includes taxes & fees
9.2/10 Wonderful! (3,526 reviews)
"It is a compact space- efficient property. Good but stiff king size bed, bathroom with a high quality shower. Love the windows and the tech associated features to it each room. amenities are early accessible. The bar and rooftop are awesome. Cleanliness is good. I guess it would’ve been nice to have ..."

Reviewed on 6 Aug. 2025

citizenM Chicago Downtown
See all 1,358 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a The Loop holiday package cost?
Much less than you might think — from as low as AU$2,249, 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.

Discover the most popular places to visit in The Loop

Millennium Park showing modern architecture, a city and street scenes

Millennium Park

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 bay or harbour, a city and a river or creek

Chicago Riverwalk

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 showing art and interior views

Art Institute of Chicago

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

Activities

River tour boat in Chicago

Architecture River Tour

AU$64
per adult
96% of travellers recommend
Architecture River Tour
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

AU$46
per adult
92% of travellers recommend
Skyline Lake Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

AU$69
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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.