Douglas Holidays from £955

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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 £1,123, price is now £955 per person
£955
per person
1 Jul - 5 Jul
found 16 hours ago
Return flight included
London (LON) to Chicago (ORD)
8.2/10 Very Good! (2,707 reviews)
The staff at Hotel Felix were kind, thoughtful, and genuinely helpful throughout my stay. The location is also a strong point — walking distance to a lot of great Chicago spots, which made getting around easy. My experience was somewhat diminished by the mandatory Urban Fee added at check-in. I understand many hotels are moving in this direction, but travelers should be aware of the additional required cost when budgeting for their stay. Outside of that, the team and location were the highlights for me.

Reviewed on 12 May 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was £1,238, price is now £991 per person
£991
per person
1 Jul - 5 Jul
found 16 hours ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
This property has a great location. The hotel was really clean! We enjoyed the bar atmosphere, and we had a delicious appetizer! I will highly recommend this location for a great getaway for couples! Page at the front desk and Prudencia in housekeeping were amazing!

Reviewed on 13 May 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was £1,242, price is now £1,041 per person
£1,041
per person
1 Jul - 5 Jul
found 16 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (3,692 reviews)
Great location. Very friendly and helpful staff.

Reviewed on 13 May 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was £1,164, price is now £981 per person
£981
per person
1 Jul - 5 Jul
found 16 hours ago
Return flight included
London (LON) to Chicago (ORD)
8.8/10 Excellent! (2,148 reviews)
Staff was very good, attentive. The property itself is in a great location, but the room showed some wear and tear - exposed drywall screws holding on bathroom door trim with some paint slapped on it, smelly sink, water damage and peeling paint on inside window sill, visually boring interior that looks like it's from the 1990's

Reviewed on 12 May 2026

L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Downtown Chicago
Price was £1,305, price is now £1,121 per person
£1,121
per person
1 Jul - 5 Jul
found 16 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (4,012 reviews)
It was clean, new, spacious and had a good common area

Reviewed on 14 May 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 £119 per night from 26 May to 27 May
£119
26 May - 27 May
includes taxes & fees
8/10 Very Good! (10,118 reviews)
The room had an odor and eventhoufh it’s a landmark building with some renovations, there were not enough outlets, no coffee pot just sat on table nowhere near an outlet to plug up and make coffee. Complimentary water should be available not just $5 bottle in room. The hallways need air freshener. ...

Reviewed on 14 May 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is £127 per night from 25 May to 26 May
£127
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (5,173 reviews)
Hotel is a beautiful, smaller boutique property.

Reviewed on 14 May 2026

River Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £153 per night from 25 May to 26 May
£153
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (4,144 reviews)
This was my first time staying in a Riu Hotel and I was incredibly impressed. It was super clean, the staff was really helpful, and the breakfast was awesome. Five stars!!

Reviewed on 14 May 2026

Hotel Riu Plaza Chicago
See all 4,669 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
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Beach Holidays
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Family Friendly Holidays

Frequently asked questions

How much does a Douglas travel package cost?
Discover the best of Douglas from just £955. 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 acclaimed art galleries and fascinating museums 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
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

£16
per child
98% of travellers recommend
Flyover in Chicago
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.