Chatham Vacations from $194

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Your Chatham Vacation

Book a Chatham vacation package and experience the way of life and vibe of this captivating neighborhood. With all your travel plans taken care of, the only thing you need to concentrate on here is having an absolute ball. Your trip to Chatham wouldn't be complete without a visit to major attractions nearby such as Abbott Park, A. Philip Randolph Pullman Porter Museum and Bronzeville Childrens Museum. No matter what your dream Chatham vacation looks like, you can turn it into reality with Expedia.

The Latest Chatham Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $367, price is now $194 per person
$194
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
This is the perfect hotel centrally located in the middle of everything. The room was super clean and the breakfast was superb! This is my new favorite Chicago hotel.

Reviewed on Oct 22, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $603, price is now $323 per person
$323
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.

Reviewed on Oct 16, 2025

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $460, price is now $280 per person
$280
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (39 reviews)
We were there for a Bachelorette party and the hotel was at a great location for it! We could walk to so many nice restaurants and shops! The hotel staff was super friendly as well!

Reviewed on Oct 15, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,117, price is now $680 per person
$680
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The kitchen was VERY clean and very well stocked. Our room was as nice as any room as I have ever stayed in. The Hotel Manager and Pablo, the Director of Rooms, were outstanding!!! they were truly a credit to the Trump brand. I have stayed at the Trump International and would stay there again in a heartbeat.

Reviewed on Oct 20, 2025

The Blackstone, Autograph Collection

The Blackstone, Autograph Collection

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $557, price is now $350 per person
$350
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,003 reviews)
Fabulous hotel we will be back

Reviewed on Oct 20, 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

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
$143 nightly
The price is $168 total per night from Nov 9 to Nov 10
$168 total
Nov 9 - Nov 10
Total with taxes and fees
7.8/10 Good! (9,545 reviews)
Average

Reviewed on Oct 22, 2025

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
$114 nightly
The price is $134 total per night from Nov 16 to Nov 17
$134 total
Nov 16 - Nov 17
Total with taxes and fees
8.8/10 Excellent! (3,128 reviews)
Good

Reviewed on Oct 22, 2025

Hilton Chicago/Magnificent Mile Suites
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $100 total per night from Nov 10 to Nov 11
$100 total
Nov 10 - Nov 11
Total with taxes and fees
7.8/10 Good! (2,498 reviews)
Great Vibe!

Reviewed on Oct 19, 2025

Freehand Chicago
See all 4,363 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
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Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Chatham

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

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

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 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
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

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

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

$44
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

$45
per adult
100% of travellers recommend
Chicago Sightseeing River and 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.