Kenwood Holidays
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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
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.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
Magnificent Mile
A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Theatre District
While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).
Top hotels in Kenwood
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
S$161
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,288 reviews)
"Lower price$"
Reviewed on 11 Aug, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
S$218
30 Aug - 31 Aug
includes taxes & fees
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
Fully refundableReserve now, pay when you stay
S$313
10 Sept - 11 Sept
includes taxes & fees
9/10 Wonderful! (2,764 reviews)
"Overall, I’d give my stay about a 3.8/5. There were some good things, but also quite a few areas that could use improvement. The room was really small, and the bathroom felt like it was in a closet — very cramped. The furniture and everything in the room also felt pretty old and worn. The closet ..."
Reviewed on 11 Aug, 2026
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.
Stay near popular Kenwood attractions
Obama's House
10.0/10 (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.
Barack Obama Residence
You can find out about the history of Chicago with a stop at Barack Obama Residence. Stroll along the beautiful beaches in this family-friendly area or visit its top-notch restaurants.
Former Home of Muhammad Ali
Find out about the history of Chicago when you spend time at Former Home of Muhammad Ali. Stroll along the lakeside or experience the fascinating museums in this vibrant area.
49th Street Beach
Why not spend a lazy afternoon at 49th Street Beach during your trip to Chicago? Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.
Hyde Park Art Center
Enjoy an outing to Hyde Park Art Center during your stay in Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.
Little Black Pearl Academy
Walk around the campus at Little Black Pearl Academy during your stay in Chicago. Wander through the lakeside and beautiful beaches in this family-friendly area.
Muddy Waters’ House
Find out about the history of Chicago when you spend time at Muddy Waters’ House. Experience the acclaimed theatre scene and fascinating museums in this vibrant area.
Jessie 'Ma' Houston Park
You can take time to visit Jessie 'Ma' Houston Park during your travels to Chicago. Wander through the lakeside and beautiful beaches in this family-friendly area.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
S$32
per adult
90% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
S$52
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.