Kenwood Vacation Packages
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Top Holiday Package Deals in Kenwood
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
CA $704
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
We absolutely loved this hotel. My wife and I came for two days to celebrate my birthday. The location is fantastic to walk many great places, breakfast buffet was the best, excellent selection and tasty. While eating breakfast then brought me a birthday brownie and put chocolate in our room. Above and beyond expectations. Very clean and modern hotel with great staff. Roof top bar is a must!
Reviewed on Sep 2, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,698
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
The Trump Hotel In Chicago is one of my family's FAVORITE hotels in the world. We stay at The Trump every single time we're in Chicago. It's the BEST.😀👍
Reviewed on Sep 2, 2026
Freehand Chicago
Downtown Chicago
CA $2,050
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
7.8/10 Good! (3,367 reviews)
Pros - this hotel is conveniently located and its less expensive than some others in the area.
Cons - the first room I was given had water damage in the ceiling and did not smell good. I also checked the AC unit and the filter was completely clogged with dust, this type of washable filter is supposed to be cleaned every month and it looks like it has at least 9+ months of dust on it. I complained about the water damage and they moved me to another room. The next room didn't have soap or shampoo in the bathroom for some reason, and I checked the air filter in this room also and it clearly hasn't been cleaned in forever. In addition to cleaning the air filters, this type of AC unit is supposed to be professionally cleaned once per year. This one has clearly not been cleaned in years.
If you want a well maintained hotel, try somewhere else.
Reviewed on Sep 2, 2026
Where to stay in Kenwood
Find the best Kenwood areas and neighborhoods for the activities you enjoy most. Learn more about Kenwood
Downtown Chicago
4 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.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Kenwood Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $141
CA $168 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very good! (10,261 reviews)
"It’s a classic Chicago hotel. It’s was clean and comfortable. Also a great location for walking to downtown parks and food!"
Reviewed on Sep 3, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $168
CA $200 total
Sep 8 - Sep 9
includes taxes & fees
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.
Frequently asked questions
How much does a Kenwood vacation package cost?
Get set to book, because a trip to Kenwood starts from only CA $704. When you bundle your hotels, flights and car rentals into a package, you'll score the biggest bargains.
How do I get a cheap travel package to Kenwood?
Browse and book everything all in one place with our Kenwood vacation packages. We have incredible bargains on hotels, flights, tours and more that'll keep your travel budget happy and adventurous side satisfied. And, with more than 550 air carriers and 1,000,000 properties globally to pick from, you'll have the flexibility to mix and match.
Where should I stay in Kenwood?
Urban adventurers come from far and wide to see University of Chicago and Chicago Museum of Science and Industry in Kenwood. Book yourself a room within walking distance of these popular attractions and visit them at your leisure.
What are the top hotels in Kenwood?
Get your escape off to a fantastic start by staying at Best Western Plus Hyde Park Chicago Hotel. It's one of most popular properties in Kenwood. Another leading option is Chicago Lake Shore Hotel.
How far in advance should I book my Kenwood vacation?
It's difficult to pick the perfect time for airfares, but we usually say the earlier, the better. Most international journeys on Expedia become available up to a year in advance. If you're booking late, don't stress. Low prices occasionally appear within a few weeks of departure dates.
What does an Expedia Kenwood travel package include?
With Expedia, you can choose a combination of car rentals, hotels and flights to build your ideal Kenwood package. Once you've made your booking, you can add on all the fun stuff like tours and activities. Remember — the more you bundle, the more discounts you'll get!
What should I know before booking a Kenwood travel package?
You'll save plenty with an Expedia travel package. Bundle your flights, rental cars and hotels and enjoy exciting discounts. Hotels aren't your only option, though. Book with us and choose from beachfront villas, creek-side mountain cabins and even glamping tents!
Can I choose my airline with a Kenwood Expedia vacation package?
Expedia offers access to more than 550 partner airlines globally, so you certainly can. Simply choose the carrier you want and craft your ideal Kenwood getaway.
If I'm not able to travel, can I cancel my Kenwood vacation package?
Don't worry if you're rethinking your Kenwood vacation package — it's possible to cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your airline, hotel or car rental company. We totally get that your circumstances can suddenly change, so look up our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.
Stay near popular Kenwood attractions
Barack Obama Residence
You can find out about the history of Chicago when you stop by Barack Obama Residence. Stroll along the beautiful beaches in this family-friendly area, or check out its top-notch restaurants.
49th Street Beach
Why not spend a lazy afternoon at 49th Street Beach during your trip to Chicago? Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.
Hyde Park Art Center
Enjoy an outing to Hyde Park Art Center during your stay in Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.
Little Black Pearl Academy
Explore the campus of Little Black Pearl Academy during your visit to Chicago. Wander the lakeside and beautiful beaches in this family-friendly area.
Muddy Waters’ House
Find out about the history of Chicago when you spend time at Muddy Waters’ House. Experience the acclaimed theater scene and fascinating museums in this vibrant area.
Kam Isaiah Israel Congregation
You can find out about the history of Chicago with a stop at Kam Isaiah Israel Congregation. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.
Jessie 'Ma' Houston Park
You can take time to visit Jessie 'Ma' Houston Park during your travels to Chicago. Wander the lakeside and beautiful beaches in this family-friendly area.
Rainbow-PUSH Headquarters
Learn about the local history of Chicago with a stop at Rainbow-PUSH Headquarters. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.
Things to do
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $56
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.