Douglas Park Holidays

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  • Better together

    Save up to S$134 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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 which includes 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

Top hotels in Douglas Park

Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$247 per night from 31 Jan to 1 Feb
S$247
31 Jan - 1 Feb
includes taxes & fees
8.4/10 Very Good! (2,526 reviews)
Great staff, comfortable room, beautiful hotel

Reviewed on 13 Jan, 2026

Hilton Chicago
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
The price is S$135 per night from 1 Feb to 2 Feb
S$135
1 Feb - 2 Feb
includes taxes & fees
8.8/10 Excellent! (3,678 reviews)
Room and hotel overall very clean. Noted some things that could be updated in bathroom(stopper in sink didnt go all the way down, peeling caulk and some missing grout). Minor updates. Our sink was clogged when we checked in and I called the front desk, housekeeping and the hotel hotline 4 different ...

Reviewed on 7 Jan, 2026

Hilton Chicago/Magnificent Mile Suites
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
75 E Wacker Dr Chicago IL
The price is S$123 per night from 27 Jan to 28 Jan
S$123
27 Jan - 28 Jan
includes taxes & fees
8.6/10 Excellent! (2,051 reviews)
Great location & everyone was very helpful. Needed a fridge for medication & they set us up in a room with one.

Reviewed on 8 Jan, 2026

Club Quarters Hotel Wacker at Michigan, Chicago
See all 4,867 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.

Frequently asked questions

How much does a Douglas Park holiday package cost?
Perhaps less than you imagined — from a tempting , as a matter of fact! By bundling hotels, flights and car rentals into your own custom-made holiday 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 holiday 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 Centre 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 holiday?
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 holiday 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 holiday package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines globally. Our holiday 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 holiday 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.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place showing a high rise building and a city

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

Things to do

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

S$57
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

S$32
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

S$51
per adult
92% of travellers recommend
Art Institute of Chicago
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.