Kenwood Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ฿4,531 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Where to stay in Kenwood

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

Downtown Chicago

5 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

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 ฿6,078 per night from 14 Sept to 15 Sept
฿6,078
฿7,135 total
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (8,984 reviews)
"Great location! Quiet and comfortable room. Love the history and architectural charm of this classic Chicago Hotel! Exercise room was the best equipped I've used!"

Reviewed on 14 Aug 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ฿5,603 per night from 2 Sept to 3 Sept
฿5,603
฿7,385 total
2 Sept - 3 Sept
includes taxes & fees
8.4/10 Very Good! (1,849 reviews)
"5 star rating! The vibe of the hotel is amazing and you can’t beat the location."

Reviewed on 11 Aug 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ฿4,642 per night from 3 Sept to 4 Sept
฿4,642
฿5,449 total
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (3,675 reviews)
"Hotel was quiet. Room was comfortable. Location was great."

Reviewed on 13 Aug 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,500 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 holiday 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 holiday 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 holiday?
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 holiday 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 holiday package?
Don't worry if you're rethinking your Kenwood holiday 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

฿1,358
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

฿1,474
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

฿1,327
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.