Douglas Park Vacation Packages

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Your Douglas Park Vacation

From its highlights to its hidden treasures, this city is best explored with a Douglas Park vacation package. Find somewhere to stay in Magnificent Mile, which is great for cafes, shopping and history. Fill your schedule with tours of University of Illinois Chicago, United Center and Credit Union 1 Arena, some of the top attractions you just have to see during a trip to Douglas Park. Browse Expedia's extensive range of travel options and start organizing your perfect vacation to Douglas Park today.

Top Holiday Package Deals in Douglas Park

Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Price was CA $1,002, price is now CA $655 per person
CA $655
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,890 reviews)
Gorgeous lobby. Wonderful dining options.

Reviewed on Aug. 29, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,066, price is now CA $1,229 per person
CA $1,229
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump

Reviewed on Aug. 29, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,375, price is now CA $820 per person
CA $820
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Very impressive, 5 star quality for 4 star prices. Highly recommend.

Reviewed on Aug. 30, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $2,190, price is now CA $1,400 per person
CA $1,400
per person
Oct 3 - Oct 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on Aug. 22, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was CA $1,133, price is now CA $740 per person
CA $740
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (282 reviews)
The staff were excellent

Reviewed on Aug. 21, 2025

Where to stay in Douglas Park

Find the best Douglas Park areas and neighborhoods for the activities you enjoy most. Learn more about Douglas Park
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 Park Hotel Deals

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Sep 4 to Sep 5
CA $207
CA $244 total
Sep 4 - Sep 5
includes taxes & fees
8.2/10 Very Good! (1,226 reviews)
"It was very close to navy pier where it was just a 10 min way. And had a great view from our room. Facing the lake"

Reviewed on Aug. 27, 2025

The Wade
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $194 per night from Sep 1 to Sep 2
CA $194
CA $228 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (9,045 reviews)
"Very convenient to South Loop sites!"

Reviewed on Aug. 26, 2025

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
The price is CA $231 per night from Sep 3 to Sep 4
CA $231
CA $271 total
Sep 3 - Sep 4
includes taxes & fees
8.4/10 Very Good! (4,802 reviews)
"Very nice,everything is around.Highly recommend."

Reviewed on Aug. 27, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,834 properties in Douglas Park
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.
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All Inclusive Vacations
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Frequently asked questions

How much does a Douglas Park vacation package cost?
Perhaps less than you imagined — from a tempting CA $655, as a matter of fact! By bundling hotels, flights and car rentals into your own custom-made vacation package, your trip to Douglas Park is just clicks away.
How do I get a cheap travel package to Douglas Park?
Bundle your hotels and flights, add on extras such as activities or a rental car, and save with a Douglas Park vacation package. You won't just land impressive discounts on your trip — you'll have plenty of choice at your fingertips too. When you book through Expedia, you can choose from more than 550 airlines and 1,000,000 properties all over the world. Your next epic adventure starts right here, right now!
Where should I stay in Douglas Park?
With lots to explore in Douglas Park, we recommend you book a hotel near its attractions. University of Illinois Chicago, United Center and Anna and Frederick Douglass Park are some interesting ones to put on your itinerary.
How far in advance should I book my Douglas Park vacation?
While not all air carriers release ticket prices early, it's usually possible to start comparing international fares on Expedia up to 12 months in advance. This is the time when you can score some fantastic deals. If you've left everything to the last minute, there's a chance you could get lucky. Sometimes the lowest prices appear just weeks before departure.
What does an Expedia Douglas Park travel package include?
That depends on what kind of getaway you have in the works. Douglas Park vacation deals can include hotels, flights and car rentals. You can mix and match to find the travel package that suits your budget and style. You can also add on experiences and activities after you've booked to pick up even bigger discounts.
What should I know before booking a Douglas Park travel package?
You can save a tidy sum by combining your hotels, airfares and rental cars. Once you've created your package, you can add on tours and activities. Your next unforgettable adventure is only a couple of clicks away.
Can I choose my airline with a Douglas Park Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines globally. Our vacation packages give you the freedom to pick from available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Douglas Park vacation package?
You can cancel your Douglas Park booking if your plans have changed. Whether you'll incur a fee or not depends on your hotel, airline or car rental company. It may be possible to cancel or change your booking free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.

Discover the most popular places to visit in Douglas Park

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

CA $57
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

CA $56
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

CA $62
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.