Kenwood Holidays from AU$3,052

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Your Kenwood Holiday

History, walking, food, good times — you'll find all that and more in Kenwood. Experience the very best of this neighbourhood with a customised holiday package to Kenwood. Kick off your trip to Kenwood by checking out nearby attractions such as University of Chicago, Chicago Museum of Science and Industry and Guaranteed Rate Field. Whatever your travel goals or the size of your budget, booking the ultimate Kenwood holiday is easy with Expedia.

Top Holiday Package Deals in Kenwood

Price found within the past 48 hours. Click for updated prices.
LakeWood Inn & Suites

LakeWood Inn & Suites

2 out of 5
Price was AU$3,140, price is now AU$3,052 per person
AU$3,052
per person
2 July - 8 July
found 15 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
7.2/10 Good! (73 reviews)
Property was nice...exactly what i expected...beds were great..slept like a baby

Reviewed on 20 Oct 2025

The Morris Estate

The Morris Estate

4 out of 5
Price was AU$4,651, price is now AU$4,107 per person
AU$4,107
per person
2 July - 8 July
found 15 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
10/10 Exceptional! (128 reviews)
Had a great stay! Great place!

Reviewed on 4 May 2026

The Brewery Lodge Hotel

The Brewery Lodge Hotel

3.5 out of 5
Price was AU$3,852, price is now AU$3,593 per person
AU$3,593
per person
2 July - 8 July
found 15 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (831 reviews)
Everything was great other than the bed being super hard. It felt cozy like I was staying at someone’s grandmas house.

Reviewed on 11 May 2026

Holiday Inn Express Hotel & Suites Niles by IHG

Holiday Inn Express Hotel & Suites Niles by IHG

2.5 out of 5
Price was AU$3,684, price is now AU$3,526 per person
AU$3,526
per person
2 July - 8 July
found 15 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (749 reviews)
Staff and breakfast was great.

Reviewed on 27 Apr 2026

Our guide on 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

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

Our pick of the best Kenwood Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is AU$219 per night from 26 May to 27 May
AU$219
26 May - 27 May
includes taxes & fees
8/10 Very Good! (10,220 reviews)
The bar being open late is nice and the staff are very helpful.

Reviewed on 12 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$272 per night from 25 May to 26 May
AU$272
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (4,125 reviews)
Very clean and spacious! Friendly staff Generous breakfast tho coffee could be much better ditto tea…both like dishwater if British take t-bags! If coffee fan have elsewhere. And no water in rooms after first night. Apart from those niggles beds very comfy enjoyable stay…roof top bar a must!

Reviewed on 12 May 2026

Hotel Riu Plaza Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
The price is AU$214 per night from 25 May to 26 May
AU$214
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (4,284 reviews)
Hotel looks better on website, not as I expected. Overall it is okay but would probably try a different hotel on my next visit.

Reviewed on 12 May 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,561 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.
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Frequently asked questions

How much does a Kenwood holiday package cost?
Get set to book, because a trip to Kenwood starts from only AU$3,052. 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.

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$38
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

AU$61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

AU$56
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.