Kenwood Vacations from ￥348,264

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    Save up to ￥109,000 when you book a flight and hotel together*

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The Latest Kenwood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was ￥411,576, price is now ￥348,264 per person
￥348,264
per person
Aug 23 - Aug 27
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,035 reviews)
One of the best places we’ve ever stayed. We had an amazing view of downtown Chicago from our floor, and our executive suite was clean and comfortable. We thoroughly enjoyed our stay and would definitely come back. The customer service and our room were excellent.

Reviewed on Jul 20, 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 ￥484,062, price is now ￥399,850 per person
￥399,850
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (2,603 reviews)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥424,244, price is now ￥351,058 per person
￥351,058
per person
Aug 23 - Aug 27
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,714 reviews)

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥495,654, price is now ￥417,180 per person
￥417,180
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9/10 Wonderful! (3,674 reviews)
Great location, nice showers. No closets in the room.

Reviewed on Jul 21, 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was ￥460,312, price is now ￥392,862 per person
￥392,862
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9/10 Wonderful! (1,443 reviews)
Our train arrived early and the allowed us to check in 2 hrs early at no charge. Staff was friendly. View from the rooftop was beautiful and the complimentary happy hour and Sunday breakfast was a great touch that was very much appreciated! Would definitely stay here again, perfect location to walk to everything downtown.

Reviewed on Jul 21, 2026

Where to stay in Kenwood

Find the best Kenwood areas and neighborhoods for the activities you enjoy most. Learn more about Kenwood
A busy city street with tall buildings, a bus, and cars.

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.

Find hotels in Downtown Chicago

Kenwood Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
The price is ￥30,714 per night from Aug 6 to Aug 7
￥30,714
￥35,008 total
Aug 6 - Aug 7
includes taxes & fees
Hyatt Regency O'Hare Chicago
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 ￥29,886 per night from Aug 9 to Aug 10
￥29,886
￥35,535 total
Aug 9 - Aug 10
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥48,590 per night from Aug 9 to Aug 10
￥48,590
￥57,772 total
Aug 9 - Aug 10
includes taxes & fees
8.6/10 Excellent! (1,941 reviews)
"There wasn’t any Clean linen available upon request. Sheets / Towels etc. The Breakfast Menu/ Bar was great."

Reviewed on Jul 20, 2026

The Wade
See all 4,413 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.

Frequently asked questions

How much does a Kenwood vacation package cost?
Get set to book, because a trip to Kenwood starts from only ￥348,264. 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

Obama's House

10.0/10 (2 reviews)
Find out about the history of Chicago when you spend time at Obama's House. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥4,389
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,992
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

￥6,502
per adult
92% of travellers recommend
Art Institute of Chicago
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.