Douglas Vacations from $462

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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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $704, price is now $462 per person
$462
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Beautiful room, great location. Will definitely stay there again.

Reviewed on Jan 28, 2026

La Banque Hotel

La Banque Hotel

4 out of 5
Price was $1,047, price is now $540 per person
$540
per person
Apr 22 - Apr 28
found 1 hour ago
Roundtrip flight included
Houston (HOU) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

Stay One Chicago

Stay One Chicago

2 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,941, price is now $1,250 per person
$1,250
per person
Apr 22 - Apr 28
found 4 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
No reviews
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $779, price is now $514 per person
$514
per person
Apr 22 - Apr 28
found 4 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
8.8/10 Excellent! (253 reviews)
I don't have any real complaints about the hotel, room or any of the facilities. Everything went as planned and without issues. My room was spacious, clean and comfortable. I would consider staying here again for business travel. The area is not the best and it shows, it is a little sketchy and you need to be aware of your surroundings, especially as you enter or exit the facility. This is outside the control of the hotel, but it should be considered if you have family traveling with you. The hotel has good safety measures in place and controlled entry, which is nice. Overall I will stay here again and recommend it for individual business travel.

Reviewed on Nov 8, 2025

4BR Corporate Suite Central and Modern

4BR Corporate Suite Central and Modern

2 out of 5
Near North Side
Save 100% on your flight
Price was $1,983, price is now $1,317 per person
$1,317
per person
Apr 22 - Apr 28
found 1 hour ago
Roundtrip flight included
Houston (HOU) to Chicago (ORD)
10/10 Exceptional! (8 reviews)
Everything was very clean organize and very well explained, we have some dificulties trying to open the garage door, but the front desk lady help us 😀 she was suoer nice and attentive, it was a very good stayed and a very beautiful place..

Reviewed on Jan 24, 2026

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
$91 nightly
The price is $107 total per night from Jan 31 to Feb 1
$107 total
Jan 31 - Feb 1
Total with taxes and fees
8/10 Very Good! (9,832 reviews)
Yes perfectly clean

Reviewed on Jan 24, 2026

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
$107 nightly
The price is $125 total per night from Feb 8 to Feb 9
$125 total
Feb 8 - Feb 9
Total with taxes and fees
8.4/10 Very Good! (5,616 reviews)
Friendly desk staff, clean room. Fridge didn't have temp adjuster and contents froze, bottles broke.

Reviewed on Jan 28, 2026

Embassy Suites by Hilton Chicago Downtown River North
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $182 total per night from Feb 4 to Feb 5
$182 total
Feb 4 - Feb 5
Total with taxes and fees
8.4/10 Very Good! (2,585 reviews)
My stay was truly amazing. Thank you and appreciate the hotel hospitality

Reviewed on Jan 25, 2026

Hilton Chicago
See all 4,857 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

Chicago El Train at The 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

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

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

Things to do

Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$61
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago Blackhawks Ice Hockey Game at United Center

Chicago Blackhawks Ice Hockey Game at United Center

$67
per adult
Chicago Blackhawks Ice Hockey Game at United Center
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.