Old Town Triangle Holidays from NZ$2,594

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Top Holiday Package Deals in Old Town Triangle

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was NZ$3,219, price is now NZ$2,594 per person
NZ$2,594
per person
22 Dec - 27 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
18.8/10 Exceptional! (1,128 reviews)
Staff was our favorite part! Very very professional and friendly

Reviewed on 14 Nov 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was NZ$4,299, price is now NZ$2,678 per person
NZ$2,678
per person
22 Dec - 27 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
17.6/10 Exceptional! (1,074 reviews)
Great trip! Will stay again.

Reviewed on 2 Nov 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was NZ$4,549, price is now NZ$3,265 per person
NZ$3,265
per person
23 Dec - 28 Dec
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
18.8/10 Exceptional! (1,773 reviews)
It was absolutely wonderful. We were upgraded to a suite which was pretty sweet (no pun intended)! At night the surrounding view of the lake along the lakeside of the hotel was spectacular. The Rebar on the mezzanine floor with a live musician playing a saxophone on a Saturday, was a cozy and lively setting. Welcome champagne upon check in was a nice touch. The Terrace 16 restaurant/bar also served scrumptious choices on the menu. Overall, very satisfied with our stay.

Reviewed on 14 Nov 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was NZ$4,432, price is now NZ$3,407 per person
NZ$3,407
per person
22 Dec - 27 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend!

Reviewed on 20 Oct 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was NZ$3,323, price is now NZ$2,689 per person
NZ$2,689
per person
22 Dec - 27 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.

Reviewed on 9 Nov 2025

Our guide on where to stay in Old Town Triangle

Find the best Old Town Triangle areas and neighborhoods for the activities you enjoy most. Learn more about Old Town Triangle
Downtown Chicago featuring a city

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.

Find hotels in Downtown Chicago

Our pick of the best Old Town Triangle Hotel Deals

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$197 per night from 25 Nov to 26 Nov
NZ$197
25 Nov - 26 Nov
includes taxes & fees
8.4/10 Very Good! (5,232 reviews)
Clean room. Super friendly front desk staff. Complimentary drinks were a big plus! Whole property was amazing. Walking distance to everything.

Reviewed on 12 Nov 2025

Embassy Suites by Hilton Chicago Downtown River North
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 NZ$263 per night from 24 Nov to 25 Nov
NZ$263
24 Nov - 25 Nov
includes taxes & fees
8.4/10 Very Good! (2,045 reviews)
What a fun hotel.... Most hoping place in town.

Reviewed on 9 Nov 2025

Palmer House a Hilton Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$203 per night from 7 Dec to 8 Dec
NZ$203
7 Dec - 8 Dec
includes taxes & fees
8.8/10 Excellent! (3,284 reviews)
Amazing

Reviewed on 14 Nov 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,615 properties in Old Town Triangle
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 an Old Town Triangle holiday package cost?
The cheapest Old Town Triangle package is NZ$2,594, so the trip of your dreams can become a reality — without a hefty price tag. Bundle flights, hotels, car rentals and more to tailor a package suited to your travelling style.
How do I get a cheap travel package to Old Town Triangle?
Combining your flight and hotel with Expedia won't just save valuable time — it'll save you a few dollars too. An Old Town Triangle holiday package makes it simple to create your dream adventure. With more than 550 airlines around the world to choose from, finding flights that fit your busy schedule won't be a challenge. In addition to that, we've got over 1 000 000 properties globally to choose from. Now that's what we call choice. No matter who you are, Expedia can show you the world.
Where should I stay in Old Town Triangle?
Take the leg work out of sightseeing by staying just a stone's throw away from Old Town Triangle's biggest attractions. Wrigley Field and Lincoln Park Zoo are two of the best in the area.
What are the top hotels in Old Town Triangle?
Whether you plan to stay for just one night or a week in Old Town Triangle, you'll get a great night's sleep at Hotel Lincoln, part of JdV by Hyatt. This place is a top pick for many travellers.
How far in advance should I book my Old Town Triangle holiday?
It's hard to pick the best time for airfares, but we normally say the earlier, the better. Plenty of international flights on Expedia become available up to 12 months in advance. If you're booking late, don't fret. Low prices occasionally appear within a few weeks of departure dates.
What does an Expedia Old Town Triangle travel package include?
That depends on you. You can select from a range of Old Town Triangle packages, such as a rental car, hotel and flight. You can also book a hotel and a flight, or a rental car and a flight. Once you've made your booking, you can add the fun stuff like experiences and activities. Whatever your Old Town Triangle getaway looks like, get set to save!
What should I know before booking an Old Town Triangle travel package?
Our prices are always low. However, you'll enjoy even more bargains if you book your hotels, flights and car rentals together. With an Expedia package, you'll get transparent pricing and tons of choice.
Can I choose my airline with an Old Town Triangle Expedia holiday package?
Expedia offers access to more than 550 partner airlines globally, so you sure can! Simply select your preferred air carrier and put together the perfect Old Town Triangle trip.
If I'm not able to travel, can I cancel my Old Town Triangle holiday package?
Because we know life can be unpredictable, the answer is yes. For further information, head to our Customer Service Portal. But generally speaking, if you've booked your Old Town Triangle holiday package in the last 24 hours, you may be able to cancel or change it free of charge. Your airline, hotel or car rental company may charge a fee if your booking is older than that.

Activities

River tour boat in Chicago

Architecture River Tour

NZ$85
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

NZ$76
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

NZ$43
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.