Douglas Vacations from $372

Book a Hotel + Flight or Car together to unlock savings

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.
Baymont by Wyndham Chicago/Alsip

Baymont by Wyndham Chicago/Alsip

2.5 out of 5
Save 100% on your flight
Price was $585, price is now $372 per person
$372
per person
Oct 8 - Oct 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (MDW)
8/10 Very Good! (1,006 reviews)
My stay was pretty good, staff were very friendly, and the hotel room was clean. I didn’t indulge in the complimentary breakfast, however, it smelled good every morning. Unfortunately, the walls are pretty thin and you can hear everything. Some guests smelled like weed even though marijuana is prohibited. Also a very few guests were playing loud music and walking up and down the hallway. My only advice would be to be careful since anybody can book a stay there.

Reviewed on Sep 2, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,110, price is now $1,258 per person
$1,258
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!

Reviewed on Sep 2, 2025

La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $885, price is now $533 per person
$533
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (434 reviews)
Very nice hotel. Would definitely stay there again!

Reviewed on Aug 26, 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was $877, price is now $543 per person
$543
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,975 reviews)
Great location. The rooms are small.

Reviewed on Sep 2, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,197, price is now $751 per person
$751
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
Parking too expensive.

Reviewed on Sep 3, 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

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$170 nightly
The price is $200 total per night from Sep 4 to Sep 5
$200 total
Sep 4 - Sep 5
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
$184 nightly
The price is $216 total per night from Sep 22 to Sep 23
$216 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
8.2/10 Very Good! (1,156 reviews)
"I enjoyed the location"

Reviewed on Aug 29, 2025

The Wade
See all 4,724 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

Walk around the campus at Illinois Institute of Technology during your visit to Chicago. Experience the acclaimed theater 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 fascinating museums.

Ida B Wells House

Things to do

River tour boat in Chicago

Architecture River Tour

$41
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

$41
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.