Douglas Vacations from ￥332,626

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  • Better together

    Save up to ￥109,000 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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The Latest Douglas Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was ￥383,936, price is now ￥332,626 per person
￥332,626
per person
Dec 22 - Dec 29
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,572 reviews)
Everything very nice it is centered where u can go to a lot of attractions

Reviewed on Nov 10, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥451,391, price is now ￥358,848 per person
￥358,848
per person
Dec 22 - Dec 29
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥427,255, price is now ￥353,562 per person
￥353,562
per person
Dec 22 - Dec 29
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,962 reviews)

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was ￥449,685, price is now ￥374,363 per person
￥374,363
per person
Dec 22 - Dec 29
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.

Reviewed on Nov 8, 2026

L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Downtown Chicago
Price was ￥381,967, price is now ￥332,876 per person
￥332,876
per person
Dec 22 - Dec 29
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (5,074 reviews)
Location is very convenient and staff are courteous and helpful.

Reviewed on Nov 10, 2026

Where to stay in Douglas

Find the best Douglas areas and neighborhoods for the activities you enjoy most. Learn more about Douglas
A cityscape with tall skyscrapers and a historic tower.

Downtown Chicago

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Douglas Hotel Deals

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 ￥18,345 per night from Nov 22 to Nov 23
￥18,345
￥21,812 total
Nov 22 - Nov 23
includes taxes & fees
8/10 Very Good! (10,170 reviews)
"the location was perfect right across from millinial park close to all tourist attractions trains busses food etc. Hotel very old it was hot in room had to keep window open all time the handle for turning on the shower came off. There was a weird smell in hall ways gym was very dirty there are parts ..."

Reviewed on Nov 11, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥17,996 per night from Nov 22 to Nov 23
￥17,996
￥21,398 total
Nov 22 - Nov 23
includes taxes & fees
8/10 Very Good! (2,696 reviews)
"Very clean ans nice hotel"

Reviewed on Nov 11, 2026

The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is ￥16,749 per night from Dec 10 to Dec 11
￥16,749
￥19,914 total
Dec 10 - Dec 11
includes taxes & fees
8.8/10 Excellent! (5,614 reviews)
"Room was cleaned and nicely kept up. Convenient location and nice view of the river."

Reviewed on Nov 10, 2026

River Hotel
See all 4,482 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 vacation package cost?
Tailor make your Douglas vacation package from as little as ￥332,626. 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 vacation 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 vacation 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 vacation?
It can be difficult to know exactly when the best time is to book your Douglas vacation. 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 vacation rentals such as beachside villas and spacious residences. You've got loads of choices!
Can I choose my airline with a Douglas Expedia vacation 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 vacation 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 vacation 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.

Stay near popular Douglas attractions

Illinois Institute of Technology

7.0/10 (4 reviews)
Walk around the campus at Illinois Institute of Technology during your visit to Chicago. Experience the acclaimed art scene and fascinating museums in this vibrant area.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥3,809
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

￥6,269
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

￥6,636
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
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.