Douglas Vacations from $366
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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 Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $866, price is now $526 per person
$526
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
the only issue i had it was that they didn’t do room service in the room, no new towels , no toilet paper and stuff like that
Reviewed on Jun 12, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,245, price is now $854 per person
$854
per person
Jul 22 - Jul 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9/10 Wonderful! (484 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,378, price is now $964 per person
$964
per person
Aug 26 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
The fitness center & spa was top notch. The on site restaurant had amazing food and service.
Reviewed on Jun 12, 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
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.
Douglas Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $158 total per night from Jun 29 to Jun 30
$158 total
Jun 29 - Jun 30
Total with taxes and fees
8/10 Very Good! (10,253 reviews)
"It's a very unique and different hotel, however, it's in a historic building, so you will learn to understand it's uniqueness."
Reviewed on Jun 13, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
$146 nightly
The price is $174 total per night from Jun 30 to Jul 1
$174 total
Jun 30 - Jul 1
Total with taxes and fees
7.8/10 Good! (1,569 reviews)
"I"
Reviewed on Jun 12, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $154 total per night from Jun 28 to Jun 29
$154 total
Jun 28 - Jun 29
Total with taxes and fees
8.8/10 Excellent! (2,656 reviews)
"I really liked it and recommend it."
Reviewed on Jun 12, 2026
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.
Stay near popular Douglas attractions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.