Chatham Vacations from $365

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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.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $597, price is now $365 per person
$365
per person
Nov 12 - Nov 15
found 15 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
9.4/10 Exceptional! (434 reviews)
Very nice hotel. Would definitely stay there again!

Reviewed on Aug 26, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $1,466, price is now $748 per person
$748
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
I loved the location - it was very walkable and lots of restaurants/shops nearby. The room itself was average - beds were very low and the furniture was kind of odd - mostly plywood built ins. But the one room served it's purpose and was clean. The issue was, I had reserved TWO rooms, but when I arrived I was informed they only had one room for me. Apparently they didn't accept the second room reservation... Neither the Emily nor Expedia notified me that one of my "PREPAID" rooms was not reserved. There were NO rooms available in the Hotel for Saturday, nor in the entire city of Chicago on Labor Day weekend, so we were left scrambling to find a place to accomodate the six of us (i.e friends couches, etc.). Not sure which company is ultimately to blame, but needless to say, ALWAYS double check your reservation with this place before you travel.

Reviewed on Sep 3, 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $913, price is now $537 per person
$537
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.

Reviewed on Aug 21, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Save 100% on your flight
Price was $1,012, price is now $614 per person
$614
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,103 reviews)
easy going to downtown, airport… Thanks for the convenient experience

Reviewed on Sep 1, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $782, price is now $477 per person
$477
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,342 reviews)
Have stay at multiple Riu hotel in my many travel. Always a great value. Their breakfast is exceptional and the service is always above average.

Reviewed on Sep 4, 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
$179 nightly
The price is $210 total per night from Sep 22 to Sep 23
$210 total
Sep 22 - Sep 23
Total with taxes and fees
Congress Plaza Hotel
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
$182 nightly
The price is $214 total per night from Sep 22 to Sep 23
$214 total
Sep 22 - Sep 23
Total with taxes and fees
Embassy Suites by Hilton Chicago Downtown River North
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $196 total per night from Sep 22 to Sep 23
$196 total
Sep 22 - Sep 23
Total with taxes and fees
The Wade
See all 4,387 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
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
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$45
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

$45
per adult
96% 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.