Douglas Holidays from AU$1,788

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Your Douglas Holiday

Make travel planning easier by locking in a holiday package to Douglas. We'll handle the small stuff, so you can focus on savouring everything this neighbourhood 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 Centre are excellent places to start. No matter your travel goals or budget, booking your ideal Douglas holiday is easy with Expedia.

Top Holiday Package Deals in Douglas

Price found within the past 48 hours. Click for updated prices.
Grand Royal Hotel O'Hare - Chicago

Grand Royal Hotel O'Hare - Chicago

3.5 out of 5
Price was AU$2,701, price is now AU$1,788 per person
AU$1,788
per person
19 Feb - 22 Feb
found 11 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
5.8/10 (215 reviews)
Friendly front desk, easy and convenient for my overnight layover in Chicago

Reviewed on 7 Nov 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was AU$3,209, price is now AU$2,099 per person
AU$2,099
per person
19 Feb - 22 Feb
found 11 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Stayed prior to flight, clean, quiet room!

Reviewed on 13 Jan 2026

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Price was AU$2,982, price is now AU$1,966 per person
AU$1,966
per person
19 Feb - 22 Feb
found 11 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,404 reviews)
The sweetest staff ever! Very welcoming. Had a great stay!

Reviewed on 9 Jan 2026

Comfort Inn & Suites Arlington Heights - Schaumburg

Comfort Inn & Suites Arlington Heights - Schaumburg

3 out of 5
Price was AU$2,771, price is now AU$1,831 per person
AU$1,831
per person
19 Feb - 22 Feb
found 11 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
8.4/10 Very Good! (782 reviews)
Everything was excellent but they need to fix the Elevator the last time l was there in October its broken

Reviewed on 6 Jan 2026

DoubleTree by Hilton Chicago Schaumburg

DoubleTree by Hilton Chicago Schaumburg

4 out of 5
Price was AU$2,807, price is now AU$1,861 per person
AU$1,861
per person
19 Feb - 22 Feb
found 11 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
7.2/10 Good! (1,003 reviews)
Hot water issue. Goy only Luke warm

Reviewed on 10 Jan 2026

Our guide on where to stay in Douglas

Find the best Douglas areas and neighborhoods for the activities you enjoy most. Learn more about Douglas
Downtown Chicago featuring 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

Our pick of the best Douglas Hotel Deals

Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$272 per night from 1 Feb to 2 Feb
AU$272
1 Feb - 2 Feb
includes taxes & fees
8.4/10 Very Good! (2,523 reviews)
Yes great Hotel everything was perfect

Reviewed on 12 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 AU$141 per night from 25 Jan to 26 Jan
AU$141
25 Jan - 26 Jan
includes taxes & fees
8.8/10 Excellent! (3,691 reviews)
Yes

Reviewed on 11 Jan 2026

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
The price is AU$287 per night from 23 Jan to 24 Jan
AU$287
23 Jan - 24 Jan
includes taxes & fees
8.4/10 Very Good! (2,243 reviews)
Clean, attractive classic looking room and bathroom.

Reviewed on 13 Jan 2026

Palmer House a Hilton Hotel
See all 4,776 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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Douglas holiday package cost?
Tailor make your Douglas holiday package from as little as AU$1,788. Pick from any combination of hotels, flights and rental cars to craft the escape you've been dreaming of. Remember to add on a few experiences or activities!
How do I get a cheap travel package to Douglas?
It's easy. Just bundle. Hotels, rental cars and flights — combine whatever you need into a Douglas holiday package and save. Score even more discounts when you include extras such as experiences or tours to your booking. But that's not the only impressive part. You have the freedom to tailor your trip your way. We offer over 550 airlines and 1 000 000 hotel options globally, so that everyone has an opportunity to travel and live out those holiday dreams.
Where should I stay in Douglas?
Urban explorers come from near and far to experience University of Chicago and Chicago Museum of Science and Industry in Douglas. Book yourself a room close to these popular attractions to make sightseeing easy.
What are the top hotels in Douglas?
Get your trip off to a flying start by booking a stay at Mccormick Place Guest House. It's one of most popular properties in Douglas. Another leading option is Villa Dubois Guest House.
How far in advance should I book my Douglas holiday?
It can be difficult to know exactly when the best time is to book your Douglas holiday. But generally the earlier you book, the cheaper the prices. In some cases, you can lock in your flights and hotels up to a year prior to departure. If you're considering a last-minute getaway, no need to fret! There are terrific deals popping up on Expedia every day.
What does an Expedia Douglas travel package include?
Flights, hotels and a shiny set of wheels for all your road trip adventures. Simply pick and choose your preferred bundle and get access to great discounts. Once you've made your booking, add on a couple of tours and experiences and watch your savings stack up. When it comes to crafting your Douglas trip, you're in control!
What should I know before booking a Douglas travel package?
Booking all the parts of your trip together is an excellent way to save. Bundle your car rentals, airfares and hotels into a neat little package. But hotels aren't your only option. Expedia features all sorts of properties, including holiday homes such as beachside villas and spacious residences. You've got loads of choices!
Can I choose my airline with a Douglas Expedia holiday package?
Yes, you can. We have more than 550 partner airlines all over the world, so choose the carrier that's a good fit for your travel needs.
If I'm not able to travel, can I cancel my Douglas holiday package?
Yes, you can. We get that things don't always go to plan, so we're here to help if you have to make changes to your Douglas holiday package. You may be able to cancel or change your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.

Activities

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$37
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

AU$60
per adult
92% of travellers recommend
Art Institute of Chicago
Lineup with Capone and Dillinger!

Chicago Crime and Mob Bus Tour

AU$73
per adult
92% of travellers recommend
Chicago Crime and Mob Bus 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.