The Loop Holidays
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- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
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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
4 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.
Magnificent Mile
An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Streeterville
Navy Pier and Michigan Avenue are just a few worthwhile attractions to visit in Streeterville. Travellers also love the fascinating museums, panoramic lake views and popular shops.
Our pick of the best The Loop Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
NZ$205
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,314 reviews)
"Great location, serious service and sanitation failures. Rooms are dated, which could be charming. The TV has basic channels only, so bring a Chromecast or Roku. The in room tablet is useless; that money should have gone to the TVs. Room service never came. I ordered biscuits and gravy and pancakes. ..."
Reviewed on 25 Aug 2026
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
Fully refundableReserve now, pay when you stay
NZ$459
7 Sept - 8 Sept
includes taxes & fees
River Hotel
75 East Wacker Drive Chicago IL
NZ$289
8 Sept - 9 Sept
includes taxes & fees
8.8/10 Excellent! (5,448 reviews)
"Rooms are VERY dated. Staff was great, but I will not be staying there again. The hotel could really invest in a refresh of the lobby area, workout room, and rooms. I think a staff member told me that it had never been renovated. So, someone needs to think about doing that."
Reviewed on 25 Aug 2026
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.
Stay near popular The Loop attractions
Chicago Riverwalk
9.6/10 (13,574 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.
Millennium Park
9.4/10 (30,446 reviews)
See mind-bending sculptures, a musically-inspired lawn and giant water fountains that double-up as video screens.
Art Institute of Chicago
9.4/10 (7,898 reviews)
The Art Institute Of Chicago's far-ranging and brilliant collections make it one of the world’s finest art museums.
Willis Tower
9.0/10 (9,893 reviews)
The Willis Tower is at its best when you're dangled over one of its glass-bottomed balconies 396 metres above Chicago.
Photo by © Choose Chicago
Chicago Theatre
9.0/10 (1,866 reviews)
See a stage show at this iconic cultural beacon, which still captures all the splendor of a trip to the movie theater in the early 20th century.
Cloud Gate
9.4/10 (104 reviews)
You can learn about the history of Chicago with a visit to Cloud Gate. Discover the entertainment choices and notable monuments in this vibrant area.
Buckingham Fountain
9.2/10 (1,301 reviews)
This enormous art deco installation gives free regular water and light shows symbolizing the power and might of Lake Michigan.
Chicago Cultural Center
9.2/10 (220 reviews)
Enjoy a stop at Chicago Cultural Center, an entertaining place to visit in Chicago. Discover the fascinating museums and notable monuments in this vibrant area.
Activities
Chicago: Navy Pier Centennial Wheel Ticket
NZ$42
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.