Chatham Vacations from ￥93,126
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The Latest Chatham Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥193,537
per person
Nov 25 - Nov 29
found 22 hours ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
This is one of the best Trump properties I've been to.
I know Trump Hotels' bar is high, but this is on another level.
Obviously, being a landmark in Chicago, location is the best in Chicago.
There is a Langham property right next to it, but this is it.
Rooms are well maintained, and the restaurants were excellent.
I hope to visit again soon.
Reviewed on Oct 12, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
￥134,441
per person
Nov 25 - Nov 29
found 22 hours ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
The Riu was great. I especially liked their attention to low-energy use. And, yes, like other commenters stated, the breakfast was plentiful.
Reviewed on Oct 12, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
￥133,892
per person
Nov 25 - Nov 29
found 22 hours ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Wonderful experience from start to finish! The staff was amazing - everyone from the valet and front desk to the rooftop restaurant employees was incredibly friendly and welcoming, as was the breakfast server in the restaurant in the lobby. The hotel was very clean, and we felt safe and secure throughout our stay. Would absolutely stay here again!
Reviewed on Oct 12, 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
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.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Chatham Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
￥16,542
￥19,668 total
Nov 10 - Nov 11
includes taxes & fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
￥22,741
￥27,037 total
Oct 25 - Oct 26
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
￥22,634
￥26,907 total
Nov 1 - Nov 2
includes taxes & fees
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 Chatham vacation package cost?
Starting from just ￥93,126, 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.
Things to do
Skydeck Chicago at Willis Tower
￥6,642
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.