Chatham Vacation Packages

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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
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
Amazing amenities. friendly staff and clean rooms. Views from the balcony were so nice!

Reviewed on Jul. 12, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I love Virgin air and expected a 5-star experience. Hotel checkin was not all that welcoming, but efficientl. They had no valet service and basically told us we were on our own. Thought ok I need a drink so went to the rooftop bar. An afterthought at this hotel. Cushions were dirty and faded. Barely staffed. More like a rooftop bar in costs rica than downtown Chicago. Room was nice and stylish. The highlight of the stay tbh as was the coffee shop.

Reviewed on Jul. 13, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Amazing customer service

Reviewed on Jul. 13, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Superb customer service, clean hotel!

Reviewed on Jun. 13, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Nice property, very walkable. Front desk was great. Bar area nice & welcome drink nice. Concierge was not around. Got suite with 2 full baths which was awesome with teens. Great stay overall!

Reviewed on Jul. 12, 2025

Where to stay in Chatham

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

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

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 $202 per night from Aug 5 to Aug 6
CA $202
CA $238 total
Aug 5 - Aug 6
includes taxes & fees
7.8/10 Good! (8,957 reviews)
"Good stay"

Reviewed on Jul. 13, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is CA $273 per night from Aug 10 to Aug 11
CA $273
CA $364 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (2,031 reviews)
"Great location ! Small but nice room ."

Reviewed on Jul. 13, 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $206 per night from Aug 10 to Aug 11
CA $206
CA $242 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (2,425 reviews)
"Great location and rooms are spacious and clean."

Reviewed on Jul. 11, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,286 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 $688, 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.

Discover the most popular places to visit in Chatham

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Navy Pier

Navy Pier

4.5/5(459 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

4.5/5(19 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue

Things to do

River tour boat in Chicago

Architecture River Tour

CA $67
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
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.