Douglas Holidays from £1,140

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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 Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,517, price is now £1,140 per person
£1,140
per person
2 May - 9 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Great place to stay the young lady checking us in was not very friendly. Never received my complimentary drinks. There was never anyone at the bar. Valet guy was very helpful!!! Other than the small things it was a good stay!!!

Reviewed on 29 Mar 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,387, price is now £1,516 per person
£1,516
per person
2 May - 9 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Great breakfast for the price. A true gem for downtown Chicago. The only bad thing I experienced was the gentleman standing outside side the front doors smoking pot every night. He was a person staying at the RIU. I was there to see a Dr at Northwestern for my rare heart and lung condition and that smell was not good for my heart or lungs

Reviewed on 30 Mar 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,682, price is now £1,816 per person
£1,816
per person
30 May - 6 Jun
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Amazing experience will be back soon

Reviewed on 29 Mar 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was £2,414, price is now £1,722 per person
£1,722
per person
30 May - 6 Jun
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Room was clean, I loved that it had robes, amazing view, and couldn’t hear much noise from other rooms. One thing I will say was that it smelled humid when we arrived nothing too crazy.

Reviewed on 30 Mar 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,860, price is now £2,099 per person
£2,099
per person
2 May - 9 May
found 6 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Thank you for your exceptional hospitality

Reviewed on 29 Mar 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

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

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 £102 per night from 5 Apr to 6 Apr
£102
5 Apr - 6 Apr
includes taxes & fees
8/10 Very Good! (10,018 reviews)
The toilet was running and I had to adjust the flapper. The hotel was great, otherwise. What could be improved is a complimentary breakfast, although I know it will increase the price on your stay.

Reviewed on 30 Mar 2026

Congress Plaza Hotel
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 £108 per night from 6 Apr to 7 Apr
£108
6 Apr - 7 Apr
includes taxes & fees
9/10 Wonderful! (4,022 reviews)
The room was pretty clean. Thermostat appeared not to be working because the temperature of the room did not change in 3 days we were there despite trying to cool it down. Continuous fan would blow but no ac. This wasn't a problem really in march, but in the summer I imagine it would be. Our room ...

Reviewed on 30 Mar 2026

Hilton Chicago/Magnificent Mile Suites
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
Fully refundableReserve now, pay when you stay
The price is £127 per night from 6 Apr to 7 Apr
£127
6 Apr - 7 Apr
includes taxes & fees
8.6/10 Excellent! (5,801 reviews)
Great location, friendly staff, complimentary full breakfast, evening drinks and snacks. A great place to stay with a family!

Reviewed on 30 Mar 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,649 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.
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Frequently asked questions

How much does a Douglas travel package cost?
Discover the best of Douglas from just £1,140. 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.

Popular places to visit

SR Crown Hall

Find out about the history of Chicago with a stop at SR Crown Hall. Experience the fascinating museums and acclaimed art galleries in this vibrant area.

SR Crown Hall

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture 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. Flight-inclusive packages are ATOL protected.