Douglas Holidays from £910

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Packages with flights are ATOL protected

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.
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Price was £1,254, price is now £910 per person
£910
per person
10 Sept - 15 Sept
found 5 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.6/10 Exceptional! (629 reviews)
It was lovely. Everyone is very nice and the breakfast was well beyond an ordinary hotel breakfast

Reviewed on 26 Jun 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,504, price is now £1,033 per person
£1,033
per person
10 Sept - 15 Sept
found 15 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
8.2/10 Very good! (2,797 reviews)
Location was excellent. Rooms were a little smaller than I'd prefer but we got by.

Reviewed on 29 Jun 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was £1,754, price is now £1,225 per person
£1,225
per person
10 Sept - 15 Sept
found 15 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.2/10 Wonderful! (1,330 reviews)
Clean and Helpful Staffs. You have to look for your parking space, mostly are street parking, but there is a valet at the hotel if you asked for it.

Reviewed on 28 Jun 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was £1,797, price is now £1,298 per person
£1,298
per person
10 Sept - 15 Sept
found 15 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.2/10 Wonderful! (1,013 reviews)
Not for family it will work for chilling with your ex or old friends

Reviewed on 29 Jun 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
Price was £1,591, price is now £1,159 per person
£1,159
per person
10 Sept - 15 Sept
found 15 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Clean room and staff was great.

Reviewed on 28 Jun 2026

Where to stay in Douglas

Find the best Douglas areas and neighborhoods for the activities you enjoy most. Learn more about Douglas
A busy city street with tall buildings, a bus, and cars.

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 £134 per night from 1 Jul to 2 Jul
£134
1 Jul - 2 Jul
includes taxes & fees
8/10 Very good! (10,166 reviews)
"Charm"

Reviewed on 29 Jun 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is £163 per night from 5 Jul to 6 Jul
£163
5 Jul - 6 Jul
includes taxes & fees
9.2/10 Wonderful! (1,833 reviews)
"Staff was extremely friendly and helpful! Very clean and inviting environment!"

Reviewed on 29 Jun 2026

Omni Chicago 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 £152 per night from 6 Jul to 7 Jul
£152
6 Jul - 7 Jul
includes taxes & fees
9/10 Wonderful! (4,480 reviews)
"I liked how they answered all my questions and was super nice to our out of town group."

Reviewed on 29 Jun 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,523 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 £910. 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

7.0/5 (4 reviews)
Explore the campus of Illinois Institute of Technology as part of your travels around Chicago. Experience the fascinating museums and acclaimed theatre scene in this vibrant area.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
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.