Armour Square Holidays from NZ$2,818

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Top Holiday Package Deals in Armour Square

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$3,760, price is now NZ$2,818 per person
NZ$2,818
per person
31 Oct - 5 Nov
found 9 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The WIt was everything. The Roof at the Wit, was amazing, be sure to make reservations. I love this hotel and Chicago it was safe and close to everything!!

Reviewed on 26 Sept 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was NZ$5,759, price is now NZ$3,908 per person
NZ$3,908
per person
31 Oct - 5 Nov
found 9 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
It’s was very clean and safe

Reviewed on 27 Sept 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was NZ$4,292, price is now NZ$3,151 per person
NZ$3,151
per person
31 Oct - 5 Nov
found 9 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
The Emily Hotel was in a convenient area of Chicago close to the family wedding we were attending in mid-September. Rooms were clean modern and had loads of desk space but no dressers or nightstands. Staff was helpful in telling us about the nearby parking garage beneath the Google building across the street. We parked our car there for $57/ day vs Valet for $85 (with unlimited in and) at The Emily. We would stay there again.

Reviewed on 26 Sept 2025

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was NZ$3,867, price is now NZ$2,900 per person
NZ$2,900
per person
31 Oct - 5 Nov
found 9 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
Always a pleasure to stay here!

Reviewed on 27 Sept 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was NZ$5,761, price is now NZ$4,372 per person
NZ$4,372
per person
31 Oct - 5 Nov
found 10 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Great place to stay.

Reviewed on 20 Sept 2025

Our guide on where to stay in Armour Square

Find the best Armour Square areas and neighborhoods for the activities you enjoy most. Learn more about Armour Square
Downtown Chicago featuring 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

Our pick of the best Armour Square 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
7.8/10 Good! (9,307 reviews)
"Parking situation is ridicules, hallways carpet very filthy. I understand it’s an older hotel but needs to be kept up. Bathroom door didn’t even close."

Reviewed on 25 Sept 2025

Get rates
Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$299 per night from 30 Sept to 1 Oct
NZ$299
30 Sept - 1 Oct
includes taxes & fees
7.8/10 Good! (2,388 reviews)
"It felt cozy and comfortable. The room was a little bit dusty and the night light was not working."

Reviewed on 24 Sept 2025

Freehand Chicago
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$327 per night from 20 Oct to 21 Oct
NZ$327
20 Oct - 21 Oct
includes taxes & fees
8.8/10 Excellent! (2,962 reviews)
"Hotel was very nice but the parking was ridiculous, $80 for valet parking per day. Luckily a staff member directed us to a parking garage right across the street for $45. There is a lot to see within walking distance. Some of the staff weren't very friendly."

Reviewed on 25 Sept 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,560 properties in Armour Square
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 Armour Square holiday package cost?
Starting from as low as NZ$2,818, you can tailor your Armour Square package the way you want. Simply bundle flights, hotels and car rentals and we'll reward you with discounts.
How do I get a cheap travel package to Armour Square?
You'll save a ton of money if you combine your hotels, car rentals and flights into an Armour Square travel package. Sometimes cheap packages mean fewer options. But not with Expedia. We offer over 550 partner airlines and 1 000 000 hotels across the world, which means you'll always have plenty of variety to choose from. Like to save even more? Add some fun activities to your package deal and unlock even more bargains! After all, travel is about more than just getting to your destination.
Where should I stay in Armour Square?
Most visitors who travel to Armour Square include University of Chicago and Chicago Museum of Science and Industry on their must-see lists. Why not consider a hotel that's close to these great attractions?
How far in advance should I book my Armour Square holiday?
Reserving your flight early with Expedia means one less thing to worry about. A number of air carriers advertise tickets up to 12 months prior to take off. This is usually the cheapest time to book. If circumstances have left you booking late, fantastic last-minute deals to Armour Square will sometimes occur just a few weeks before departure.
What does an Expedia Armour Square travel package include?
You can select from a combination of rental cars, flights and hotels. Once you've made your booking, you can add the fun stuff like tours and experiences. Want to pick your airfare class? That's possible too. The choice is yours when it comes to putting together your dream Armour Square trip.
What should I know before booking an Armour Square travel package?
Discover deals that suit your budget with an Expedia package. Hotels, flights, rental cars — we have everything you need to plan your escape. You'll save big dollars just by bundling your bookings. Whether you're heading away on an adventure in the snow or sunning yourself on a warm beach, your dream getaway is just clicks away.
Can I choose my airline with an Armour Square Expedia holiday package?
Yes, you're in control. We offer more than 550 airlines all over the world, so you can design your Armour Square trip according to your travel preferences.
If I'm not able to travel, can I cancel my Armour Square holiday package?
You can. We realise even the best-laid plans can go awry, so we're happy to help if you have to make changes to your Armour Square holiday package. It may be possible to cancel or amend your itinerary for free if you've booked in the last 24 hours. Your hotel, airline or car rental company may impose a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.