Kenilworth Vacation Packages

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Your Kenilworth Vacation

When you book a Kenilworth vacation package, it's all about enjoying your adventure to the fullest. Delve into the highlights of this fun-filled city knowing that all the travel planning has been taken care of in advance. Fill your schedule with visits to Chicago Botanic Garden, The Glen Club and North Shore Center for the Performing Arts, some of the top attractions you shouldn't miss during your trip to Kenilworth. Stop dreaming and start doing. Check out the broad range of options on Expedia today and put your Kenilworth vacation plans into gear!

Top Kenilworth Vacation Deals

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

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,478, price is now CA $993 per person
CA $993
per person
Aug 5 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,332 reviews)
Very good Outstanding service

Reviewed on May 19, 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 $1,872, price is now CA $1,252 per person
CA $1,252
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,507 reviews)
I’m not sure if the hotel had a lack of staff but I called for towels and never received any, the next day they brought towels shortly after I called again.

Reviewed on May 21, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,763, price is now CA $1,251 per person
CA $1,251
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,126 reviews)
Great staff and perfect place to be in the middle of everything!

Reviewed on Apr 27, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,292, price is now CA $1,638 per person
CA $1,638
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,864 reviews)
Great experience! Would stay here agin

Reviewed on May 18, 2026

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Price was CA $1,558, price is now CA $1,118 per person
CA $1,118
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (2,795 reviews)
Very clean and friendly staff

Reviewed on May 17, 2026

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Kenilworth 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
per night
May 26 - May 27
8/10 Very Good! (10,123 reviews)
"Nice clean hotel downtown."

Reviewed on May 21, 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
per night
May 25 - May 26
9.4/10 Exceptional! (4,204 reviews)
"Amazing breakfast included!"

Reviewed on May 21, 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
per night
May 25 - May 26
7.8/10 Good! (1,451 reviews)
"Valet parking was terrible and I should have received a $30 discount off of the valet parking per my reservation and they charged me the full amount. Also waited over 30mins for valet to get my car"

Reviewed on May 21, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,376 properties in Kenilworth
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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Discover the most popular places to visit in Kenilworth

Wrigley Field

Wrigley Field

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

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

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

Navy Pier

What to do in Kenilworth

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 Kenilworth

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.