The Loop Holidays from NZ$2,542

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Top Holiday Package Deals in The Loop

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 11 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.4/10 Very Good! (3,410 reviews)
The hotel is a very nice area. My main complaint is that you can’t close the curtains and the beds feel old.

Reviewed on 18 Jun. 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 11 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,613 reviews)
Great hotel with great staff.

Reviewed on 20 Jun. 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 11 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (2,039 reviews)
Exceptional service from beginning to end, everyone was so friendly. The rooms were lovely, very spacious and the beds were great. I especially loved the key security for the elevators and lights, nice touch. Everything was extremely clean; the elevators smelled wonderful. The breakfast on the second floor was amazing! We will definitely stay here again.

Reviewed on 20 Jun. 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 11 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (319 reviews)
I had no idea how nice this property would be! I had a full one-bedroom apartment and amazing view and amenities. 10/10, would stay again!

Reviewed on 1 Jun. 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 11 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,087 reviews)
Great setup, location

Reviewed on 21 Jun. 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

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

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 NZ$281 per night from 3 July to 4 July
NZ$281
3 July - 4 July
includes taxes & fees
7.8/10 Good! (8,858 reviews)
"The room air conditioning did not cool the room and the lighting for the restroom was poor , hard to do makeup."

Reviewed on 20 Jun. 2025

Congress Plaza Hotel
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$241 per night from 2 July to 3 July
NZ$241
2 July - 3 July
includes taxes & fees
9.2/10 Wonderful! (3,196 reviews)
"clean and conveniently located. throughly enjoyed my stay here, will be staying at another citizenm in the future."

Reviewed on 19 Jun. 2025

citizenM Chicago Downtown
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 NZ$350 per night from 1 July to 2 July
NZ$350
1 July - 2 July
includes taxes & fees
8.8/10 Excellent! (2,251 reviews)
"Amazing, clean. Bed was phenomenal"

Reviewed on 20 Jun. 2025

Swissotel - Chicago
See all 1,237 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 NZ$2,542, 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)

See mind-bending sculptures, a musically-inspired lawn and giant water fountains that double-up as video screens.

Millennium Park
Art Institute of Chicago showing art and interior views

Art Institute of Chicago

4.5/5(32 reviews)

The Art Institute Of Chicago's far-ranging and brilliant collections make it one of the world’s finest art museums.

Art Institute of Chicago
Willis Tower showing interior views, views and city views

Willis Tower

4.5/5(39 reviews)

The Willis Tower is at its best when you're dangled over one of its glass-bottomed balconies 396 metres above Chicago.

Willis Tower

Activities

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

NZ$40
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

NZ$69
per adult
96% of travellers recommend
Chicago: Architecture Boat Tour with Drinks
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

NZ$74
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
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.