Chatham Vacations from ￥337,288

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The Latest Chatham Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was ￥442,434, price is now ￥337,288 per person
￥337,288
per person
May 13 - May 18
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,719 reviews)
Great place to stay. Staff is very friendly

Reviewed on Mar 25, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was ￥619,115, price is now ￥437,907 per person
￥437,907
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Clean room, very nice front desk and great location

Reviewed on Mar 26, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was ￥495,778, price is now ￥352,488 per person
￥352,488
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
10/10 makes you feel at home. One of the best hotels I’ve ever stayed in.

Reviewed on Mar 23, 2026

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Price was ￥658,325, price is now ￥510,528 per person
￥510,528
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,675 reviews)
We loved our stay. Two adults and our eight-year-old son took a weekend trip to Chicago. This hotel was very close to the field museum and walking distance to magnificent mile. Short Uber ride to nearby shopping and Willis Tower. The staff were awesome and upgraded our room at a low price. We felt very safe and staff were very helpful. The eighth floor had a beautiful pool, spa and sauna, great view of lake mi, open late too. We dined for breakfast at yoke and Niu B for dinner. Delicious. At checkout we purchased a future Hilton grand vacation at a great discount too. Let’s go. :)

Reviewed on Mar 25, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥568,890, price is now ￥460,718 per person
￥460,718
per person
May 14 - May 18
found 5 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Perfect room size for 2+1. The river view was breathtaking especially in the late evening while serenade of colors highlighted other buildings surrounding the Trump Tower hotel. Good food at the restaurant and nice staff helping you to enjoy the memorable time during the visit. We will be back in near future for surr!

Reviewed on Mar 24, 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 showing a city

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 ￥18,424 per night from Apr 1 to Apr 2
￥18,424
￥21,629 total
Apr 1 - Apr 2
includes taxes & fees
8/10 Very Good! (9,988 reviews)
I’ve stayed here before, and this time I was disappointed at the lack of cleanliness in the room and overall condition of it.

Reviewed on Mar 26, 2026

Congress Plaza Hotel
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 ￥21,849 per night from Apr 9 to Apr 10
￥21,849
￥25,648 total
Apr 9 - Apr 10
includes taxes & fees
9/10 Wonderful! (3,984 reviews)
Please DO NOT GO HERE!! they got bed bugs!

Reviewed on Mar 26, 2026

Hilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥23,316 per night from Apr 5 to Apr 6
￥23,316
￥27,371 total
Apr 5 - Apr 6
includes taxes & fees
8.6/10 Excellent! (5,775 reviews)
The pillows in the rooms were very hard and so was the bed. In the pool area there where not enough towels for people and it seemed very cold for a indoor pool.

Reviewed on Mar 25, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,384 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.

Frequently asked questions

How much does a Chatham vacation package cost?
Starting from just ￥337,288, 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 cbd, a sporting event and a city

Wrigley Field

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

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

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
Chicago Skyline at North Beach

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥3,985
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

￥6,236
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

￥6,860
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
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.