Douglas Holidays from £1,000
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Your Douglas Holiday
Planning your next break just got a lot easier with a holiday package to Douglas. Immerse yourself in the best this neighbourhood has to offer while creating beautiful memories that'll stay with you for years. Not sure what to do and see during your trip to Douglas? Nearby attractions like Art Institute of Chicago, University of Illinois Chicago and Grant Park are great places to start. Whatever your travel plans or the size of your budget, booking your ideal Douglas holiday has never been easier with Expedia.
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
£1,000
per person
18 Dec - 23 Dec
found 19 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
We loved our stay at RIU. The hotel was walkable to Navy Pier and several great restaurants and shops. The only complaint I can think of is the bathroom door not shutting completely unless it was locked (made your shower chilly). We would definitely stay here again!
Reviewed on 2 Oct 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
4 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.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Top hotels in Douglas
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
£142
2 Nov - 3 Nov
includes taxes & fees
8.8/10 Excellent! (5,460 reviews)
"Location location Close to everything"
Reviewed on 1 Oct 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£114
1 Nov - 2 Nov
includes taxes & fees
8/10 Very good! (10,135 reviews)
"This was my first stay in the North Towers in nearly 30 years, and I really enjoyed rediscovering its character. The high ceilings, rounded corners, heavy wooden doors, and even little quirks like the light switch inside the closet were a treat. These details are increasingly rare and give the hotel ..."
Reviewed on 1 Oct 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
£128
1 Nov - 2 Nov
includes taxes & fees
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 travel package cost?
Discover the best of Douglas from just £1,000. Choose from a great selection of rental cars, hotels and flights to suit your travel style. Pick up even better deals when you add a few tours or activities to your package.
If I'm not able to travel, can I cancel my Douglas travel package?
Yes you can, and we're here to help. You may be able to cancel or change your Douglas travel package for free within 24 hours of booking. However, you may incur a fee from your hotel, airline or car rental company for older bookings. If your circumstances unexpectedly change, visit our Customer Service Portal for more information.
How do I get a cheap travel package to Douglas?
One of the simplest ways to save dollars (and time) is to bundle your bookings with Expedia. Hotels, rental cars, flights and activities — we've got everything you need. Select a combination that best suits you and watch your savings grow. We know a travel package is never one-size-fits-all. That's why we offer more than 550 airlines and 1,000,000 hotel options across the globe, which lets you customize your Douglas adventure.
Does Expedia offer Book Now, Pay Later Douglas holidays?
Expedia has teamed up with online lender Klarna to make booking your next break easier on your budget. Paying by instalment means you can spread the costs of your next dream escape, leaving you with more cash to play with while you're away. Klarna has several payment plans to choose from, so you're sure to find one that fits your budget. Check out these flexible payment options:
- Pay monthly holidays: If paying bite-sized amounts each month is something that would work for you, Klarna offers just that! Paying in convenient monthly instalments will make that dream getaway possible.
- Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay off your holiday across multiple transactions.
- Low deposit holidays: When you want to jump on an awesome deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you lock in your escape.
Where should I stay in Douglas?
Visitors come from all corners of the globe to see Millennium Park and Wrigley Field in Douglas. Book yourself a room close to these awesome attractions to make sightseeing easy.
What are the top hotels in Douglas?
Book a room at Hyatt Regency Chicago. It's one of the neighbourhood's most in-demand properties. Another well-known option in Douglas is The Godfrey Hotel Chicago.
How far in advance should I book my Douglas holiday?
While not all airlines advertise tickets early, you can usually start comparing international flights on Expedia up to a year in advance. This is the time when you can score some fantastic deals. If you're purchasing tickets last minute, you may still be in luck. Sometimes the cheapest prices appear just weeks before departure.
What does an Expedia Douglas travel package include?
It comes down to what sort of escape you're planning. Douglas holiday deals can include car rentals, flights and hotels. You can mix and match to find the travel package that suits you. You can also add on activities and experiences after you've booked to pick up even bigger discounts.
What should I know before booking a Douglas travel package?
Get ready to save with an Expedia travel package. Combine your airfares, rental cars and hotels and be rewarded with terrific discounts. Hotels aren't your only option, though. We've got beach villas, chalets in the middle of mountains and even treehouses and ranches!
Can I choose my airline with a Douglas Expedia travel package?
Yes, you're in charge. Expedia has access to more than 550 airlines all over the world, so you can design your Douglas holiday according to your budget and needs.
Stay near popular Douglas attractions
Illinois Institute of Technology
7.0/10 (4 reviews)
Explore the campus of Illinois Institute of Technology as part of your travels around Chicago. Experience the acclaimed art galleries and fascinating museums in this vibrant area.
Wabash Ave YMCA
You can find out about the history of Chicago when you stop by Wabash Ave YMCA. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
Ida B Wells House
You can find out about the history of Chicago with a visit to Ida B Wells House. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.
McCormick Tribune Center
You can find out about the history of Chicago with a visit to McCormick Tribune Center. Stroll along the lakeside or visit the notable monuments in this vibrant area.
Southside Community Arts Center
Enjoy an outing to Southside Community Arts Center during your stay in Chicago. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
Lake Meadows Park
Lake Meadows Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its fascinating museums.
Ida B. Wells-Barnett Residence
You can find out about the history of Chicago with a visit to Ida B. Wells-Barnett Residence. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
Robert W Roloson Houses
You can find out about the history of Chicago with a visit to Robert W Roloson Houses. Stroll along the lakeside or experience the fascinating museums in this vibrant area.
Things to do
Skydeck Chicago at Willis Tower
£32
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.