Kenwood Holidays

Book a Hotel + Flight or Car together to unlock savings

Where to stay in Kenwood

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

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 3.577.102 ₫ per night from 29 Jun to 30 Jun
3.577.102 ₫
4.252.817 ₫ total
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,260 reviews)
"Staff was friendly, our room was very old. Our bathroom door knob was broken and it took my daughter a long time to get me out. We called the front desk about it but nobody came the entire 5 days we stayed to fix it. The safe was locked when we got there so we had to have security come and open it ..."

Reviewed on 13 Jun 2026

Congress Plaza Hotel
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is 4.183.290 ₫ per night from 28 Jun to 29 Jun
4.183.290 ₫
4.768.114 ₫ total
28 Jun - 29 Jun
includes taxes & fees
8.8/10 Excellent! (2,663 reviews)
"Overall stay was great with my brother. I will come back agin. Staff were helpful especially with our shuttle ride to the airport."

Reviewed on 13 Jun 2026

Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is 3.797.954 ₫ per night from 30 Jun to 1 Jul
3.797.954 ₫
4.515.389 ₫ total
30 Jun - 1 Jul
includes taxes & fees
7.8/10 Good! (1,569 reviews)
"I"

Reviewed on 12 Jun 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,476 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 1null000null000 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.

Stay near popular Kenwood attractions

Obama's House

5.0/5 (2 reviews)
Find out about the history of Chicago with a stop at Obama's House. Amble around this vibrant area's lakeside or experience its fascinating museums.
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