Douglas Holidays from £840

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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.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
2 Oct - 9 Oct
found 21 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Bed was comfortable, everyone on the front desk team that i interacted with were great. I hope to be back someday.

Reviewed on 13 Aug 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
2 Oct - 9 Oct
found 21 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (654 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on 27 Jul 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
17 Sept - 22 Sept
found 10 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
24 Oct - 29 Oct
found 14 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
i’ve stayed here a few times and love it. it’s my go to, i highly recommend this place!

Reviewed on 11 Aug 2025

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
per person
2 Oct - 9 Oct
found 21 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,063 reviews)
I think that 67 dollars is a lot for a day of parking, but I guess it’s city’s fault.

Reviewed on 12 Aug 2025

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

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 £117 per night from 1 Sept to 2 Sept
£117
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (8,943 reviews)
"The hotel room was quiet and clean, only a little old and something outdated but still functional (tv). The area is great to visit a lot of the Chicago attractions and staff was helpful. Would recommend!"

Reviewed on 11 Aug 2025

Congress Plaza Hotel
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 £169 per night from 21 Aug to 22 Aug
£169
21 Aug - 22 Aug
includes taxes & fees
8.4/10 Very Good! (1,849 reviews)
"5 star rating! The vibe of the hotel is amazing and you can’t beat the location."

Reviewed on 11 Aug 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £118 per night from 2 Sept to 3 Sept
£118
2 Sept - 3 Sept
includes taxes & fees
8.4/10 Very Good! (3,658 reviews)
"Great rooms, comfortable, walking distance to anywhere you’d want to go."

Reviewed on 10 Aug 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,600 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Douglas travel package cost?
Discover the best of Douglas from just £840. 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 theatre scene in this vibrant area.

SR Crown Hall

Things to do

Chicago Private Boat Rental - Explore Chicago's Skyline & Waters

Chicago Private Boat Rental - Explore Chicago's Skyline & Waters

£1,693
per traveller
Chicago Private Boat Rental - Explore Chicago's Skyline & Waters
River tour boat in Chicago

Architecture River Tour

£31
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
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. Flight-inclusive packages are ATOL protected.