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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,483, price is now CA $994 per person
CA $994
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

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,057, price is now CA $1,243 per person
CA $1,243
per person
Sep 24 - Sep 28
found 1 day 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

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,648, price is now CA $1,089 per person
CA $1,089
per person
Sep 6 - Sep 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (128 reviews)
A hidden gem in the heart of the Gold Coast! Wonderful staff! Shout out to Steve! He made us feel right at home! Coffee machines in the room were amazing, the coffee was delicious! Thank you to all the staff for all that they do! Til next time!

Reviewed on Jul 5, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,565, price is now CA $1,710 per person
CA $1,710
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Wonderful amenities, clean and great location. The only thing I did not care for was checking myself in. Front staff welcome you but you have to complete your own check in. After a long day if travel the last thing a person wants to do is complete forms. Lowers the Luxury feel of the property when the front desk does not do what an average Holiday Inn does.

Reviewed on Jul 6, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $2,167, price is now CA $1,473 per person
CA $1,473
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)
Vas room, AC was broken, lots of dust … Old

Reviewed on Jul 7, 2026

Ready to book your vacation to Kenilworth?

 

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Kenilworth 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 27 to Jul 28
CA $233
CA $277 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very good! (1,701 reviews)
"HIDDEN FEES WILL CHARGE DOUBLE"

Reviewed on Jul 6, 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 $240 per night from Jul 9 to Jul 10
CA $240
CA $332 total
Jul 9 - Jul 10
includes taxes & fees
9.2/10 Wonderful! (1,867 reviews)
"Vas room, AC was broken, lots of dust … Old"

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 8 to Jul 9
CA $231
CA $275 total
Jul 8 - Jul 9
includes taxes & fees
8/10 Very good! (10,194 reviews)
"Bartender, Chris was very nice!"

Reviewed on Jul 6, 2026

Congress Plaza Hotel
See all 4,165 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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What to do in Kenilworth

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 Kenilworth

Frequently asked questions

How much does a Kenilworth vacation package cost?
You'll find cheap prices from CA $994 on Expedia for your Kenilworth escape. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Kenilworth costs.
What are the cheapest months to go to Kenilworth?
January, February and November are the best times to look for cheap Kenilworth vacation packages. Travelling in quieter months means you can usually find better prices on flights and hotels.
How many days is enough for Kenilworth?
With about 2 days, you'll have plenty of time to visit popular neighbourhoods such as Rogers Park and Wildwood during your Kenilworth vacation. Remember to also add The Glen Club and Baha'i House of Worship to your must-see list. Up for some more adventures? Consider exploring outside of Kenilworth on day trips and tours.
How to find the best Kenilworth package deals?
Use Expedia's handy filters to find some unbeatable Kenilworth package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Kenilworth package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Kenilworth vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component separately. And you'll still get the freedom to create a tailored Kenilworth vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Kenilworth?
If you have your Kenilworth vacation dates confirmed, book as soon as you can to snap up some unbeatable deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Kenilworth?

  1. Choose when to travel: Check your diary and pack your bags. Your preferred season and the type of activities on offer will also help you decide when to escape to Kenilworth.
  2. Set your budget: Consider costs such as flights, meals and transportation when working out how much to save for your trip to Kenilworth. Then, choose a hotel that fits your budget, whether that's a wallet-friendly option or a more luxurious retreat.
  3. Work out your trip length: Think about how much time you want to spend discovering Kenilworth. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a tailored Kenilworth vacation package.

Explore a world of travel with Expedia

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