Douglas Holidays

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    Save up to €185 when you book a flight and hotel together*

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

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Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was €848, price is now €729 per person
€729
per person
2 Apr - 5 Apr
just found
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (2,208 reviews)
Thoughtful helpful staff. Wonderful experience. Over and above our expectations.

Reviewed on 23 Jan 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was €1,086, price is now €823 per person
€823
per person
2 Apr - 5 Apr
just found
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Incredible location and wonderful satff

Reviewed on 23 Jan 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was €989, price is now €831 per person
€831
per person
2 Apr - 5 Apr
just found
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Property was clean, welcoming, pet friendly

Reviewed on 18 Jan 2026

Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
Price was €906, price is now €776 per person
€776
per person
2 Apr - 5 Apr
just found
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,159 reviews)
Room and customer service was great!

Reviewed on 20 Jan 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was €912, price is now €784 per person
€784
per person
2 Apr - 5 Apr
just found
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
The room was clean. The staff was very nice. They even held on to our stuff on our last day after check out so we could explore the town luggage free!

Reviewed on 23 Jan 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 which includes 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 €135 per night from 14 Feb to 15 Feb
€135
14 Feb - 15 Feb
includes taxes & fees
8/10 Very Good! (9,797 reviews)
Room was clean. Only interaction i had with staff is when i checked in and checked out. You should add on your advertisement, parking that you pay 62 a day for has no in and out privileges. No one rents a car to leave parked. How many times a day do i have to keep paying 62? I gave it a food rating ...

Reviewed on 20 Jan 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is €154 per night from 1 Feb to 2 Feb
€154
1 Feb - 2 Feb
includes taxes & fees
8.4/10 Very Good! (2,541 reviews)
Great staff, good location .

Reviewed on 14 Jan 2026

Hilton Chicago
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
71 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is €158 per night from 28 Jan to 29 Jan
€158
28 Jan - 29 Jan
includes taxes & fees
9.2/10 Wonderful! (3,251 reviews)
Clean room, excellent staff

Reviewed on 19 Jan 2026

The Royal Sonesta Chicago Downtown
See all 4,794 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.

Frequently asked questions

How much does a Douglas holiday package cost?
Tailor make your Douglas holiday package from as little as €729. Pick from any combination of hotels, flights and rental cars to craft the escape you've been dreaming of. Remember to add on a few experiences or activities!
How do I get a cheap travel package to Douglas?
It's easy. Just bundle. Hotels, rental cars and flights — combine whatever you need into a Douglas holiday package and save. Score even more discounts when you include extras such as experiences or tours to your booking. But that's not the only impressive part. You have the freedom to tailor your trip your way. We offer over 550 airlines and 1,000,000 hotel options globally, so that everyone has an opportunity to travel and live out those holiday dreams.
Where should I stay in Douglas?
Urban explorers come from near and far to experience University of Chicago and Chicago Museum of Science and Industry in Douglas. Book yourself a room close to these popular attractions to make sightseeing easy.
What are the top hotels in Douglas?
Get your trip off to a flying start by booking a stay at Mccormick Place Guest House. It's one of most popular properties in Douglas. Another leading option is Villa Dubois Guest House.
How far in advance should I book my Douglas holiday?
It can be difficult to know exactly when the best time is to book your Douglas holiday. But generally the earlier you book, the cheaper the prices. In some cases, you can lock in your flights and hotels up to a year prior to departure. If you're considering a last-minute getaway, no need to fret! There are terrific deals popping up on Expedia every day.
What does an Expedia Douglas travel package include?
Flights, hotels and a shiny set of wheels for all your road trip adventures. Simply pick and choose your preferred bundle and get access to great discounts. Once you've made your booking, add on a couple of tours and experiences and watch your savings stack up. When it comes to crafting your Douglas trip, you're in control!
What should I know before booking a Douglas travel package?
Booking all the parts of your trip together is an excellent way to save. Bundle your car rentals, airfares and hotels into a neat little package. But hotels aren't your only option. Expedia features all sorts of properties, including holiday rentals such as beachside villas and spacious residences. You've got loads of choices!
Can I choose my airline with a Douglas Expedia holiday package?
Yes, you can. We have more than 550 partner airlines all over the world, so choose the carrier that's a good fit for your travel needs.
If I'm not able to travel, can I cancel my Douglas holiday package?
Yes, you can. We get that things don't always go to plan, so we're here to help if you have to make changes to your Douglas holiday package. You may be able to cancel or change your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.

Popular places to visit

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.

Lake Meadows Park

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€25
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

€21
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

€34
per adult
92% of travellers recommend
Art Institute of 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.