Kenwood Trips (flight + hotel)

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    Save up to P 3,118 when you book a flight and hotel together*
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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

5 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 Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Top hotels in Kenwood

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 P8,075 per night from Aug 4 to Aug 5
P8,075
P9,479 total
Aug 4 - Aug 5
includes taxes & fees
7.8/10 Good! (8,874 reviews)
"The history of the hotel is amazing and she might be an old girl with old features but she still shines like a diamond. Plus, the lake side view cannot be beat."

Reviewed on Jul 4, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is P12,865 per night from Jul 7 to Jul 8
P12,865
P16,908 total
Jul 7 - Jul 8
includes taxes & fees
9/10 Wonderful! (1,970 reviews)
"Even after renovation rooms are still looking dated"

Reviewed on Jul 4, 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is P9,494 per night from Jul 10 to Jul 11
P9,494
P11,145 total
Jul 10 - Jul 11
includes taxes & fees
8.8/10 Excellent! (2,388 reviews)
"Grear"

Reviewed on Jul 5, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,378 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 . 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.

Things to do

River tour boat in Chicago

Architecture River Tour

P2,750
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

P2,537
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

P2,537
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
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.