Douglas Vacations from $440

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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 $812, price is now $440 per person
$440
per person
Apr 4 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
No parking available, the hotel was nice, room etc. but breakfast was overly crowded, cafeteria style. They say breakfast is free with stay but then I was charged $85. When I asked what the charge was for they said for breakfast, room service etc. plus parking was an additional $150, not on site so not too pleased with the overall experience. Staff was very nice though.

Reviewed on Jan 22, 2026

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $780, price is now $456 per person
$456
per person
Apr 4 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Room was extremely clean, and staff was very accommodating

Reviewed on Jan 17, 2026

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Save 100% on your flight
Price was $821, price is now $540 per person
$540
per person
Apr 4 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Hotel was very clean. Concierge was great with advice. Sports bar pepperoni pizza was great and the french fries were just as freshly cooked. Room was clean. Bed was great. Shower pressure great. Toilet correct height for a man of my age. Pillows…..pillows with a firmness of that of a 48 year old mother who breast fed all her 7 children until 9 months old. Glad the kids are good but those pillows need work Hilton. God Bless and safe travels to all. See you next time.

Reviewed on Jan 20, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $731, price is now $481 per person
$481
per person
Apr 4 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Everything about this hotel is special. Great staff- awesome restaurant/bar. Location is perfect. This hotel is my destination every time I come to the city. Which is quite often.

Reviewed on Jan 20, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,560, price is now $1,027 per person
$1,027
per person
Mar 13 - Mar 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Exceptional service, great location, beautiful hotel

Reviewed on Jan 20, 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
$89 nightly
The price is $104 total per night from Jan 24 to Jan 25
$104 total
Jan 24 - Jan 25
Total with taxes and fees
8/10 Very Good! (9,799 reviews)
Room was clean. Only interaction i had with staff is when i checked in and checked out. You should add on your advertisement, parking that you pay 62 a day for has no in and out privileges. No one rents a car to leave parked. How many times a day do i have to keep paying 62? I gave it a food rating ...

Reviewed on Jan 20, 2026

Congress Plaza Hotel
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 1 to Feb 2
$182 total
Feb 1 - Feb 2
Total with taxes and fees
8.4/10 Very Good! (2,555 reviews)
Did not have breakfast

Reviewed on Jan 19, 2026

Hilton Chicago
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
$106 nightly
The price is $124 total per night from Feb 9 to Feb 10
$124 total
Feb 9 - Feb 10
Total with taxes and fees
8.4/10 Very Good! (5,574 reviews)
It was clean room.. breakfast was good

Reviewed on Jan 21, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,794 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
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Discover the most popular places to visit in Douglas

Chicago El Train at The 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 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.