Chatham Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in Chatham

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,578, price is now CA $1,025 per person
CA $1,025
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,019 reviews)
The place was spacious and well decorated. Location was great and staff was friendly. We did not use the amenities but the 6th floor was amazing! The two things that could be a lot better: shower pressure and blackout curtains. I am a very light sleeper and the room was filled with daylight as early as 4:45am in June. Shower had no pressure and very little water. Overall was a great stay!

Reviewed on Jun 15, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,838, price is now CA $1,230 per person
CA $1,230
per person
Sep 3 - Sep 6
found 9 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,119 reviews)
Great staff and property!

Reviewed on Jun 10, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,631, price is now CA $1,896 per person
CA $1,896
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
If you drive, it’s very close to everything pretty much. It’s clean and nice to stay with family. Parking is a little expensive but that applies to most of Chicago area.

Reviewed on Jun 14, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $2,406, price is now CA $1,755 per person
CA $1,755
per person
Aug 1 - Aug 5
found 6 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,325 reviews)
The staff was great. The room was nice but I would have preferred more towels. The remote in our room wasn’t working fully as well as the steamer in the room. Otherwise, it is a good hotel but would not recommend for families.

Reviewed on Jun 15, 2026

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was CA $2,235, price is now CA $1,664 per person
CA $1,664
per person
Sep 3 - Sep 6
just found
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
The room was lovely and spacious. The bathroom was very nice. We ordered room service as well as had a drink and ate at the restaurant in the hotel and that was delicious.

Reviewed on Jun 15, 2026

Where to stay in Chatham

Find the best Chatham areas and neighborhoods for the activities you enjoy most. Learn more about Chatham
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

Chatham Hotel Deals

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 CA $191 per night from Jun 30 to Jul 1
CA $191
CA $227 total
Jun 30 - Jul 1
includes taxes & fees
8/10 Very Good! (10,286 reviews)
"This is the second time I’ve stayed at this property. It is conveniently located and the rooms facing the lake have a gorgeous view (request lake view). The room lighting was poor, and I missed having a table on each side of the bed."

Reviewed on Jun 16, 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $191 per night from Jun 30 to Jul 1
CA $191
CA $227 total
Jun 30 - Jul 1
includes taxes & fees
7.8/10 Good! (1,592 reviews)
"Clean room staff nice"

Reviewed on Jun 15, 2026

The Chicago Hotel Collection - Magnificent Mile
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $215 per night from Jun 30 to Jul 1
CA $215
CA $256 total
Jun 30 - Jul 1
includes taxes & fees
8.2/10 Very Good! (1,611 reviews)
"It was so relaxing. Older room but has been upgraded and was clean. Restaurant had great food."

Reviewed on Jun 15, 2026

The Chicago Hotel Collection Ambassador Gold Coast
See all 4,369 properties in Chatham
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Chatham vacation package cost?
Starting from just CA $1,025, a package is your portal to low-cost travel. Build your own Chatham getaway by choosing from our huge range of hotels, airfares and rental cars.
How do I get a cheap travel package to Chatham?
Imagine all the fun things you could do in Chatham with a wad of extra cash in your wallet. Watch your savings stack up when you bundle your hotel and flights into a Chatham vacation package. You have loads of choice when you book with Expedia too. In fact, you can take your pick of over 550 air carriers and 1,000,000 properties around the world. Whether you're vacationing with the entire family or surprising your special someone, organizing a getaway to Chatham is better with a package.
Where should I stay in Chatham?
With fascinating attractions such as Abbott Park and Bronzeville Childrens Museum in this neighborhood, see if you can find a hotel near them. Advocate Trinity Hospital is another sight that draws the crowds.
How far in advance should I book my Chatham vacation?
Earlier is always better. Airlines generally release flight tickets up to 12 months prior to departure, and this is a great opportunity to pick up some rock-bottom prices. Just been told you need to take some vacation time next month? That's alright! Expedia are never short of fantastic deals to send you off on the getaway of your dreams, at an affordable price.
What does an Expedia Chatham travel package include?
From airfares and hotels to car rentals, Expedia can help you put together a Chatham package that fits you. Heading off for a week or two? Look into a rental car, flight and hotel bundle. If your break is short, a flight and hotel deal may suit you better. Activities can also be added after you've booked. Our travel packages make it simple to plan and save.
What should I know before booking a Chatham travel package?
We already have low prices. However, you'll grab an even better deal if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll always get transparent pricing and a great range of choice.
Can I choose my airline with a Chatham Expedia vacation package?
Yes, and with more than 550 airlines to choose from around the world, you're spoiled for choice. Browse the available options and find out which airline fits your budget and needs.
If I'm not able to travel, can I cancel my Chatham vacation package?
You can. We understand that things don't always go to plan, so we're here to help if you need to make changes to your Chatham vacation package. It may be possible to change or cancel your itinerary at no cost if you've booked in the last 24 hours. Your hotel, airline or car rental company may impose a fee if your booking was made more than 24 hours ago. Head to our Customer Service Portal for more information. Also, be sure to check your itinerary for the finer details on change fees.

Stay near popular Chatham attractions

Johnson Products

Find out about the history of Chicago with a stop at Johnson Products. Amble around the area's beaches or visit its shops.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.