The Loop Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to AU$703 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    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
Downtown Chicago featuring a city

Downtown Chicago

5 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Our pick of the best The Loop Hotel Deals

River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$184 per night from 20 Apr to 21 Apr
AU$184
includes taxes & fees
20 Apr - 21 Apr
8.6/10 Excellent! (3,946 reviews)
Important review
"While their rooms are great. I have stayed with this location years ago and same.. rooms are great but in 2025 their front desk service / billing has changed. I stayed with them for 4 days extended stay same room. My advice for anyone reading this its best to book through any third party that you ..."

Reviewed on 24 Mar. 2025

River Hotel
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 AU$356 per night from 4 Apr to 5 Apr
AU$356
includes taxes & fees
4 Apr - 5 Apr
8.8/10 Excellent! (1,987 reviews)
"Went here for NYE. Perfect location to see the Navy Pier fmand Chicago River fireworks! Easy parking and super walkable..literally near EVERYTHING!"

Reviewed on 25 Mar. 2025

Swissotel - Chicago
L7 Chicago by LOTTE
L7 Chicago by LOTTE
4.5 out of 5
225 N Wabash Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$330 per night from 31 Mar to 1 Apr
AU$330
includes taxes & fees
31 Mar - 1 Apr
9.6/10 Exceptional! (1,960 reviews)
"Good location"

Reviewed on 25 Mar. 2025

L7 Chicago by LOTTE
See all 1,192 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 , 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

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
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
Art Institute of Chicago showing art and interior views

Art Institute of Chicago

4.5/5(32 reviews)

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

Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

AU$70
per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Color Factory Chicago Ticket

Color Factory Chicago Ticket

AU$54
per adult
100% of travellers recommend
Color Factory Chicago Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$34
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.