Douglas Vacations from $368

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Your Douglas Vacation

Make travel planning easier by locking in a vacation package to Douglas. We'll handle the small stuff, so you can focus on savoring everything this neighborhood has to offer. Wondering what to see and do during your trip to Douglas? Nearby attractions like Guaranteed Rate Field, Illinois Institute of Technology and Bridgeport Art Center are excellent places to start. No matter your travel goals or budget, booking your ideal Douglas vacation is easy with Expedia.

The Latest Douglas Vacation Packages

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $726, price is now $368 per person
$368
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel

Reviewed on Oct 20, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,151, price is now $457 per person
$457
per person
Dec 21 - Dec 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,070 reviews)
location to everything

Reviewed on Oct 30, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $1,010, price is now $474 per person
$474
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
We loved the Pendry!

Reviewed on Oct 27, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $746, price is now $368 per person
$368
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Loved my stay here. Everything was top notch from the time I entered the lobby. The staff was welcoming and enthusiastic about you choosing to patronize their hotel. The check-in process was quick. The hotel’s rooms were very clean and had the latest amenities. Televisions had numerous channel options. The roof top bar was amazing for photo ops. It’s also in a very good location for site seeing & shopping.

Reviewed on Oct 31, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was $796, price is now $404 per person
$404
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.

Reviewed on Oct 28, 2025

Where to stay in Douglas

Find the best Douglas areas and neighborhoods for the activities you enjoy most. Learn more about Douglas
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

Douglas Hotel Deals

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
$118 nightly
The price is $139 total per night from Nov 23 to Nov 24
$139 total
Nov 23 - Nov 24
Total with taxes and fees
8.4/10 Very Good! (5,180 reviews)
Amazing amenities, cleanness and quite space

Reviewed on Nov 1, 2025

Embassy Suites by Hilton Chicago Downtown River North
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $129 total per night from Nov 25 to Nov 26
$129 total
Nov 25 - Nov 26
Total with taxes and fees
7.8/10 Good! (9,647 reviews)
Adequate

Reviewed on Nov 1, 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $99 total per night from Nov 17 to Nov 18
$99 total
Nov 17 - Nov 18
Total with taxes and fees
7.8/10 Good! (2,551 reviews)
Room was clean and stocked with bodywash, shampoo, handsoap. Staff were courteous.

Reviewed on Oct 31, 2025

Freehand Chicago
See all 4,636 properties in Douglas
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 Douglas

Illinois Institute of Technology

Illinois Institute of Technology

3.5/5(4 reviews)

Walk around the campus at Illinois Institute of Technology during your visit to Chicago. Experience the acclaimed art scene and fascinating museums in this vibrant area.

Illinois Institute of Technology
Patterns everywhere!! This patterned wall can be found in the MTCC

McCormick Tribune Center

You can find out about the history of Chicago when you stop by McCormick Tribune Center. Stroll along the lakeside or visit the notable monuments in this vibrant area.

McCormick Tribune Center

Ida B Wells House

You can find out about the history of Chicago with a stop at Ida B Wells House. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

Ida B Wells House

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
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.