The Loop Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €185 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

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
The price is €118 per night from 1 Apr to 2 Apr
€118
1 Apr - 2 Apr
includes taxes & fees
8/10 Very Good! (9,977 reviews)
Overall, the hotel was clean, and the lounge was spacious, well-organized, and inviting. The property is a bit older, but not in a negative way—it simply has that classic feel. Our room was on the 5th floor, and the area was quiet, which made our stay very comfortable. The location is also excellent. ...

Reviewed on 21 Mar 2026

Congress Plaza Hotel
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 €198 per night from 29 Mar to 30 Mar
€198
29 Mar - 30 Mar
includes taxes & fees
9.4/10 Exceptional! (3,460 reviews)
I got woken up at 10 pm with strange noises all night coming from my room somewhere. Knocking, banging, scratching. I turned on the light and the noises would stop. Couldn’t sleep well. Felt like I was in a haunted room

Reviewed on 21 Mar 2026

Hyatt Regency Chicago
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
323 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is €161 per night from 29 Mar to 30 Mar
€161
29 Mar - 30 Mar
includes taxes & fees
9/10 Wonderful! (3,226 reviews)
We love this hotel and always stay here when needing to stay in the North Loop area. The property is dog friendly and staff is very attentive. Our daughter wished there was a pool and I a hot tub, but for the price, the room, the staff, the view and walkability it is great! There is a dog park about ...

Reviewed on 20 Mar 2026

Swissotel - Chicago
See all 1,211 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 , 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.