Douglas Vacations from $283

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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.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $439, price is now $283 per person
$283
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,862 reviews)
The staff (lobby check-in, security, and housekeeping) were the nicest employees we have ever encountered at a hotel! Also a beautiful hotel!

Reviewed on Dec 22, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $638, price is now $369 per person
$369
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Great location, clean room and friendly staff!

Reviewed on Dec 14, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $542, price is now $325 per person
$325
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Amazing close to Michigan Ave

Reviewed on Dec 24, 2025

The Drake

The Drake

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $557, price is now $364 per person
$364
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,334 reviews)
Fantastic property and great staff. We keep coming back!

Reviewed on Dec 22, 2025

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $552, price is now $366 per person
$366
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
The hotel was too notch. The staff excelled at customer service. Our favorite was Moe in Toro. We was always happy to see us, got our orders correct every time and had the best stories!!! Jo was also awesome at the bar in Toro! Thank you for the great stay!!!!

Reviewed on Dec 23, 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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $105 total per night from Jan 5 to Jan 6
$105 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
8.8/10 Excellent! (3,549 reviews)
Room was warm Recommend softer toilet paper please

Reviewed on Dec 23, 2025

Hilton Chicago/Magnificent Mile Suites
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $179 total per night from Jan 2 to Jan 3
$179 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
8.4/10 Very Good! (2,170 reviews)
Clean rooms, extremely friendly staff, onsite Starbucks, Lockwood restaurant was amazing, beautiful gathering area in the lounge. Close to all the Christmas must do’s. Decorated so so beautifully for Christmas!

Reviewed on Dec 24, 2025

Palmer House a Hilton Hotel
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $149 total per night from Jan 4 to Jan 5
$149 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.2/10 Wonderful! (2,152 reviews)
Very friendly and helpful staff

Reviewed on Dec 23, 2025

Silversmith Hotel Chicago Downtown
See all 4,728 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 fascinating museums and acclaimed theater scene 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

$44
per adult
96% of travellers recommend
Architecture River Tour
Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$80
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
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 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.