Douglas Holidays

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

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Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was €1,080, price is now €873 per person
€873
per person
16 Apr - 20 Apr
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (2,070 reviews)
Very nice & clean hotel and near the Bean and shops are walkable.

Reviewed on 3 Mar 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was €1,334, price is now €929 per person
€929
per person
16 Apr - 20 Apr
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Everything was great, except for the rooftop that was not open because which was the main reason we chose this hotel

Reviewed on 10 Mar 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €1,615, price is now €1,270 per person
€1,270
per person
16 Apr - 20 Apr
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,839 reviews)
One of the best hotels I've ever stayed at

Reviewed on 10 Mar 2026

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was €1,966, price is now €1,561 per person
€1,561
per person
4 May - 9 May
found 22 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,177 reviews)
Chris at the front desk truly went above and beyond, welcoming us with fantastic recommendations for local restaurants and attractions that made our trip even more memorable. Our room was absolutely stunning, featuring tasteful decor and exquisite artwork that created a warm, inviting ambiance. It was spotless and incredibly comfortable, making me feel right at home.

Reviewed on 6 Mar 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was €1,104, price is now €893 per person
€893
per person
16 Apr - 20 Apr
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,613 reviews)
My stay at LondonHouse Chicago was absolutely amazing from start to finish. The hotel itself is beautiful and perfectly located, offering stunning views of the river and city skyline. The restaurants were excellent, with delicious food and a great atmosphere. The rooftop experience was definitely a highlight and made the stay feel even more special. I also had the chance to visit the spa, which was incredibly relaxing and well done. The environment was peaceful, the service was top-tier, and it was the perfect way to unwind during my trip. Overall, everything—from the service to the amenities—was exceptional. I would definitely book again and highly recommend LondonHouse Chicago to anyone visiting the city. ⭐⭐⭐⭐⭐

Reviewed on 10 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 which includes a city

Downtown Chicago

4 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 €168 per night from 21 Mar to 22 Mar
€168
21 Mar - 22 Mar
includes taxes & fees
8/10 Very Good! (9,942 reviews)
I like this hotel. It’s simple, clean, no frills and gets the job done. Hallways carpets are a little worse for wear but the room serves the purpose - you get what you reserve! - and you’re close to everything. It’s a “go to” for me.

Reviewed on 10 Mar 2026

Congress Plaza 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 €163 per night from 18 Mar to 19 Mar
€163
18 Mar - 19 Mar
includes taxes & fees
9.4/10 Exceptional! (3,505 reviews)
Everything was great, except for the rooftop that was not open because which was the main reason we chose this hotel

Reviewed on 10 Mar 2026

Hotel Riu Plaza Chicago
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
The price is €123 per night from 22 Mar to 23 Mar
€123
22 Mar - 23 Mar
includes taxes & fees
8.6/10 Excellent! (5,724 reviews)
The room was perfect, the bar open up at 4pm and they have happy hour at 5:30-7 they do have a little spot to get snack they are over price but they have water if you need any in the front desk .

Reviewed on 10 Mar 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,756 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 €873. 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

€22
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

€34
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

€37
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
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.