Kenwood Vacation Packages

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Top Holiday Package Deals in Kenwood

Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 8 - Jul. 11
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (977 reviews)
The hotel was absolutely perfect for our quick weekend getaway. It was super comfortable, clean and safe. The staff was wonderful!

Reviewed on May 19, 2024

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 14 - Aug. 19
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
8.2/10 Very Good! (1,509 reviews)
Beautiful building on a beautiful park. Private as can be.

Reviewed on May 21, 2024

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 27 - Jul. 1
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Enjoyed the property and roof top pool

Reviewed on May 21, 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 1 - Aug. 6
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (3,511 reviews)
Tuve un late Checkin. Fue notificado. Me dieron una habitación diferente a la reservada. Al día siguiente tuvimos que cambiarnos, perdí lo que había comprado de comida pues no tenía donde guardarlo al dejar la habitación. Me dijeron que me darían un upgrade y me dieron una habitación exactamente como la había reservado inicialmente, además les pedí una cobija adicional Y más amenities y no las dejaron en la nueva habitación. No hubo ninguna compensación por el mal rato. El personal de front desk solo se disculpó amablemente. Esto no debería ocurrir. El hotel tiene una locación estupenda, el roof top vale la pena, el brunch nada espectacular. Pero agradable servicio.

Reviewed on May 21, 2024

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 1 - Jul. 5
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
The suite was excellent I highly recommend it was amazing I truly enjoyed everything!!!

Reviewed on May 20, 2024

Where to stay in Kenwood

Find the best Kenwood areas and neighborhoods for the activities you enjoy most. Learn more about Kenwood
Downtown Chicago showing a city

Downtown Chicago

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Grant Park and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips in Downtown Chicago

Kenwood 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 $225 per night from Jun. 16 to Jun. 17
CA $225
CA $264 total
includes taxes & fees
Jun 16 - Jun 17
7.6/10 Good! (6,786 reviews)
"Nice old hotel with a lot of history, in a beautiful area in sight of Lake Michigan."

Reviewed on May 22, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from May 28 to May 29
CA $233
CA $273 total
includes taxes & fees
May 28 - May 29
8.6/10 Excellent! (2,889 reviews)
"Staff at the front desk are really helpful and friendly"

Reviewed on May 19, 2024

River Hotel
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $171 per night from May 29 to May 30
CA $171
CA $221 total
includes taxes & fees
May 29 - May 30
7.6/10 Good! (2,602 reviews)
"I don’t really write reviews for places I stay at but this one impressed me beyond my expectations. I planned this trip for my fiancé’s 30th birthday and the location and price of this hotel is the best you will find. Not too far away from everything, conveniently located transportation and so many ..."

Reviewed on May 20, 2024

Warwick Allerton - Chicago
See all 4,027 properties in Kenwood
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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Kenwood vacation package cost?
Get set to book, because a trip to Kenwood starts from only CA $1,160. 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.

Discover the most popular places to visit in Kenwood

Image for 4944 S Woodlawn Ave

4944 S Woodlawn Ave

Find out about the history of Chicago when you spend time at 4944 S Woodlawn Ave. Stroll along the lakeside or visit the notable monuments in this vibrant area.

4944 S Woodlawn Ave
Image for Hyde Park Art Center

Hyde Park Art Center

You can enjoy some culture when you stop by Hyde Park Art Center in Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

Hyde Park Art Center
Image for Rainbow-PUSH Headquarters

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.

Rainbow-PUSH Headquarters

Things to do

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

CA $311
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Pizza Tour

Chicago Pizza Tour

CA $102
Per adult
100% of travellers recommend
Chicago Pizza Tour
Image for Chicago: City Minibus Tour with Optional Architecture Cruise

Chicago: City Minibus Tour with Optional Architecture Cruise

CA $64
Per adult
98% of travellers recommend
Chicago: City Minibus Tour with Optional Architecture Cruise
See all activities in Chicago

Other vacations you might like

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