St. Ben's Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

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

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Price found within the past 48 hours. Click for updated prices.
  • Smart TV
    Jun 27 - Jul 1

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (485 reviews)
    "Perfect stay"
    Reviewed May 20, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,457
    CA $975
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • Indoor wedding
    Aug 5 - Aug 9

    Swissotel - Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.0/10 - Wonderful (3,334 reviews)
    "Very good Outstanding service "
    Reviewed May 19, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,463
    CA $993
    per traveller
    found 1 day ago
    Swissotel - Chicago
  • Terrace/patio
    Jun 27 - Jul 1

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (2,508 reviews)
    "The breakfast menu & service at the Lyrica was excellent. The parking was very convenient, although a little pricey at $65 for overnight. The rooms and view were simply awesome. The service at the front desk was excellent. I look forward to my next stay."
    Reviewed May 20, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,870
    CA $1,271
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Lounge
    Jul 23 - Jul 26

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,126 reviews)
    "Great staff and perfect place to be in the middle of everything!"
    Reviewed April 27, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,763
    CA $1,251
    per traveller
    found 22 hours ago
    Pendry Chicago
  • Terrace/patio
    Jun 27 - Jul 1

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    4 nights
    5.0 star property
    9.4/10 - Exceptional (1,873 reviews)
    "Great experience! Would stay here agin"
    Reviewed May 18, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $2,513
    CA $1,789
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago

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
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

St. Ben's 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 $184 per night from May 26 to May 27
CA $184
CA $218 total
May 26 - May 27
includes taxes & fees
8/10 Very Good! (10,171 reviews)
"Good for a sleep and go. Not horrible, certainly not the best hotel i've ever stayed at."

Reviewed on May 20, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $205 per night from May 25 to May 26
CA $205
CA $283 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,197 reviews)
"Very nice hotel. Great Breakfast. Comfortable bed, lots of towels. Good cleaning, however could be better. Nice staff. Great location. If I return to Chicago, l’ll come back to this Hotel."

Reviewed on May 20, 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from May 25 to May 26
CA $167
CA $198 total
May 25 - May 26
includes taxes & fees
7.8/10 Good! (1,444 reviews)
"the room was clean, the staff was friendly! the rooftop bar was a bit expensive though."

Reviewed on May 20, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,732 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 . 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.

Discover the most popular places to visit in St. Ben's

Wrigley Field

Wrigley Field

4.5/5(159 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(3 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(460 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

CA $55
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
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.