The Loop Holidays from AU$600

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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.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$1,000, price is now AU$600 per person
AU$600
per person
9 Feb - 15 Feb
found 12 hours ago
Return flight included
New York (NYC) to Chicago (ORD)
9.2/10 Wonderful! (2,241 reviews)
Everyone was great. A special shout out to Tareka and Nate who worked behind the bar!

Reviewed on 16 Dec 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$2,949, price is now AU$1,659 per person
AU$1,659
per person
9 Feb - 15 Feb
found 12 hours ago
Return flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.

Reviewed on 14 Dec 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$1,159, price is now AU$672 per person
AU$672
per person
9 Feb - 15 Feb
found 12 hours ago
Return flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.

Reviewed on 8 Dec 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$1,413, price is now AU$827 per person
AU$827
per person
9 Feb - 15 Feb
found 12 hours ago
Return flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Great location, clean room and friendly staff!

Reviewed on 14 Dec 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$1,935, price is now AU$1,172 per person
AU$1,172
per person
9 Feb - 15 Feb
found 12 hours ago
Return flight included
New York (NYC) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was nice. Service was good.

Reviewed on 17 Dec 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

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$189 per night from 4 Jan to 5 Jan
AU$189
4 Jan - 5 Jan 2026
includes taxes & fees
9.2/10 Wonderful! (2,130 reviews)
Clean room, attentive staff, great lounge!

Reviewed on 15 Dec 2025

Silversmith Hotel Chicago Downtown
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
75 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$138 per night from 16 Jan to 17 Jan
AU$138
16 Jan - 17 Jan 2026
includes taxes & fees
8.6/10 Excellent! (1,988 reviews)
Very clean and the staff was wonderful!

Reviewed on 13 Dec 2025

Club Quarters Hotel Wacker at Michigan, Chicago
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$229 per night from 30 Dec to 31 Dec
AU$229
30 Dec - 31 Dec
includes taxes & fees
8.4/10 Very Good! (2,134 reviews)
Clean room. I didn’t mind the old door knobs I liked it. Smaller room than anticipated but it was nice and clean.

Reviewed on 14 Dec 2025

Palmer House a Hilton Hotel
See all 1,234 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
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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$600, 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

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

Chicago Riverwalk

4.5/5(26 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
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

4.5/5(73 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
Willis Tower showing interior views, views and city views

Willis Tower

4.5/5(39 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

Activities

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$61
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Art Institute of Chicago

Art Institute of Chicago

AU$60
per adult
92% of travellers recommend
Art Institute of Chicago
Lineup with Capone and Dillinger!

Chicago Crime and Mob Bus Tour

AU$67
per adult
92% of travellers recommend
Chicago Crime and Mob Bus 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.