Armour Square Vacation Packages

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Top Holiday Package Deals in Armour Square

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,886, price is now CA $1,182 per person
CA $1,182
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (449 reviews)
Everything was amazing from the staff to the amenities, the view and the cleanliness! I will definitely be booking again!

Reviewed on Apr 20, 2026

The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was CA $2,345, price is now CA $1,344 per person
CA $1,344
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.4/10 Very Good! (1,791 reviews)
I had a short stay, but it was truly a great experience. I only stayed for one night, and from the moment I arrived, the service was friendly and efficient. The room was clean, comfortable, and well-maintained—perfect for getting a good night’s rest. The next morning, the breakfast was definitely the highlight of my stay. Everything was fresh, delicious, and well-prepared. It was the perfect way to end my visit on a high note. I would definitely come back and highly recommend this hotel.

Reviewed on Apr 20, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $3,116, price is now CA $1,894 per person
CA $1,894
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,463 reviews)
No restaurant or available food after 10pm.

Reviewed on Apr 21, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $3,382, price is now CA $2,166 per person
CA $2,166
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (932 reviews)
10/10 highly recommend

Reviewed on Apr 21, 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was CA $2,699, price is now CA $1,752 per person
CA $1,752
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,417 reviews)
Great location and converted old Virgin Hotel. Room was fine and hotel basics were fine. There wasn’t any room service daily or for my 3 night stay. There was a strike for housekeepers and they were LOUD out front everyday. Not sure what the hotel fee was for on top of Expedia hotel charge was for, they gave me 2 waters the first day and that was it. They also upsell their vacation club/time share a lot, kinda odd.

Reviewed on Apr 14, 2026

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

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

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
The price is CA $171 per night from Apr 26 to Apr 27
CA $171
CA $200 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,164 reviews)
The room shown in the picture is not the one they put me on

Reviewed on Apr 21, 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is CA $190 per night from Apr 26 to Apr 27
CA $190
CA $223 total
Apr 26 - Apr 27
includes taxes & fees
8.8/10 Excellent! (5,109 reviews)
The

Reviewed on Apr 21, 2026

River Hotel
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
The price is CA $118 per night from Apr 26 to Apr 27
CA $118
CA $181 total
Apr 26 - Apr 27
includes taxes & fees
8.2/10 Very Good! (2,628 reviews)
The room was actually pretty good and pretty good size for two people and a queen bed I really loved it and I would go back again.

Reviewed on Apr 21, 2026

Hotel Felix River North/Magnificent Mile
See all 4,765 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does an Armour Square vacation package cost?
Starting from as low as CA $1,182, 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 vacation?
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 vacation 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 vacation package?
You can. We realize even the best-laid plans can go awry, so we're happy to help if you have to make changes to your Armour Square vacation 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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
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.