St. Ben's Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in St. Ben's

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,389, price is now CA $921 per person
CA $921
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Excellent spot, in the perfect location. Parking at the property is pretty expensive, but there are cheaper parking garages close by.

Reviewed on Jul 6, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was CA $3,926, price is now CA $2,363 per person
CA $2,363
per person
Sep 20 - Sep 23
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
We came to the property for my wife’s 40th birthday celebration. From the moment we walked in through the doors, we felt pampered. Everyone on staff was friendly, high energy, and always willing to help. The housekeeping staff was top notch as they went above and beyond with expectation on not only keeping things clean, but organizing our clutter, leaving thoughtful birthday treats, and making us feel comfortable. I now do not want to travel without staying at a 4 seasons property. They made our experience 10 times better!

Reviewed on Jul 6, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,047, price is now CA $1,235 per person
CA $1,235
per person
Sep 24 - Sep 28
found 14 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back. The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.

Reviewed on Jul 2, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $2,110, price is now CA $1,436 per person
CA $1,436
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Convenient location and friendly staff.

Reviewed on Jul 7, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,153, price is now CA $1,484 per person
CA $1,484
per person
Sep 20 - Sep 23
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,136 reviews)
Great location can get a bit noisy but really nice hotel.

Reviewed on Jul 8, 2026

Where to stay in St. Ben's

Find the best St. Ben's areas and neighborhoods for the activities you enjoy most. Learn more about St. Ben's
A busy city street with tall buildings, a bus, and cars.

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

St. Ben's Hotel Deals

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from Jul 28 to Jul 29
CA $233
CA $277 total
Jul 28 - Jul 29
includes taxes & fees
8.2/10 Very good! (1,711 reviews)
"They had extra charges, when checking in to my room. Also, the couch had stains in my room and only one of us could take a shower. The shower was plugged and filled up with water. Would not drain."

Reviewed on Jul 8, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $339 per night from Jul 26 to Jul 27
CA $339
CA $451 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (1,874 reviews)
"Convenient location and friendly staff."

Reviewed on Jul 7, 2026

Omni Chicago Hotel
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 $231 per night from Jul 9 to Jul 10
CA $231
CA $275 total
Jul 9 - Jul 10
includes taxes & fees
8/10 Very good! (10,200 reviews)
"Dated hotel but the rooms are kept clean, updated flooring and really nice bedding. Fantastic location downtown, less than a mile walking distance from Museum Campus."

Reviewed on Jul 7, 2026

Congress Plaza Hotel
See all 4,493 properties in St. Ben's
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.
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Frequently asked questions

How much does a St. Bens vacation package cost?
Chart your own course with our St. Bens vacation packages, which start from just CA $921. Choose the hotels and flights that suit your style. Then, add on one or two sightseeing activities for an amazing escape.
How do I get a cheap travel package to St. Bens?
Bundling your hotel and flight with Expedia won't just save valuable time — it'll save you cash too. A St. Bens vacation package makes it a breeze to arrange the perfect trip. With more than 550 airlines all over the world to pick from, finding flights that fit your busy schedule won't be an issue. In addition to that, we have over 1,000,000 hotel options globally to take your pick of. Talk about choice! Whatever your budget, Expedia will help show you the world.
Where should I stay in St. Bens?
Urban adventurers come from near and far to see Wrigley Field and Lincoln Park Zoo in St. Bens. Stay within a stone's throw of these must-see attractions and visit them at your leisure.
How far in advance should I book my St. Bens vacation?
While prices fluctuate, we generally recommend booking your flight as early as possible. Many international fares are found on Expedia up to 12 months in advance. If you're booking late, you might still be lucky. Cheaper tickets to St. Bens occasionally appear only weeks before departure.
What does an Expedia St. Bens travel package include?
You can choose from a combination of hotels, rental cars and flights. Once you've made your booking, you can also add on experiences and tours. Want to pick your airfare class? That's easily done too. The choice is yours when it comes to organizing your dream St. Bens escape.
What should I know before booking a St. Bens travel package?
A travel package can be customized for your budget and is an easy way to stretch your hard-earned dollars. How little or much you include is totally up to you. Hotels, rental cars and flights — mix and match whatever combination suits your style.
Can I choose my airline with a St. Bens Expedia vacation package?
With a vacation package, you're the one in charge. Whether you're looking to fly to St. Bens in first class or coach, simply choose from the available airline options. Expedia has access to over 550 airline partners throughout the world.
If I'm not able to travel, can I cancel my St. Bens vacation package?
If your vacation plans in St. Bens have changed, it's good to know that you can cancel your booking. If you made your booking in the last 24 hours, you may be eligible for a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may impose a cancellation fee. To learn more, check our Customer Service Portal.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $58
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.