The Loop Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$703 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

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.

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

Our pick of the best The Loop Hotel Deals

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$267 per night from 4 Jan to 5 Jan
AU$267
4 Jan - 5 Jan 2026
includes taxes & fees
8.4/10 Very Good! (2,176 reviews)
Room is gorgeous!!

Reviewed on 27 Dec 2025

Palmer House a Hilton 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 AU$257 per night from 4 Jan to 5 Jan
AU$257
4 Jan - 5 Jan 2026
includes taxes & fees
8.4/10 Very Good! (2,417 reviews)
Check in staff were great and room was clean. Worst part was house cleaner knocking at door at 1030am, after being up till 2am night before have a good time at football game. Hot tub amazing and our view!

Reviewed on 27 Dec 2025

Hilton Chicago
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$143 per night from 10 Jan to 11 Jan
AU$143
10 Jan - 11 Jan 2026
includes taxes & fees
8.6/10 Excellent! (2,014 reviews)
Easy check in. Ready to upgrade. I love how central it is and the water stations on each floor. This is our second time to stay here and will do it again!

Reviewed on 23 Dec 2025

Club Quarters Hotel Wacker at Michigan, Chicago
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 , 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

Activities

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