Douglas Vacations from ￥354,982

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    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.
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Downtown Chicago
Price was ￥419,064, price is now ￥354,982 per person
￥354,982
per person
Jul 19 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (2,216 reviews)
Our suite lights didn’t work.

Reviewed on May 11, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was ￥463,528, price is now ￥380,494 per person
￥380,494
per person
Jul 19 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (471 reviews)
The rooms were very clean!

Reviewed on May 4, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥433,054, price is now ￥359,343 per person
￥359,343
per person
Jul 19 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (4,070 reviews)
Very clean and spacious! Friendly staff Generous breakfast tho coffee could be much better ditto tea…both like dishwater if British take t-bags! If coffee fan have elsewhere. And no water in rooms after first night. Apart from those niggles beds very comfy enjoyable stay…roof top bar a must!

Reviewed on May 12, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ￥463,306, price is now ￥386,848 per person
￥386,848
per person
Jul 19 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (472 reviews)
Love the amenities. Great location too

Reviewed on May 3, 2026

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was ￥500,842, price is now ￥425,272 per person
￥425,272
per person
Jul 19 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,225 reviews)
Professional, friendly staff. Nicely furnished room, very quiet and clean. Great stay

Reviewed on May 11, 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

Douglas Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is ￥20,994 per night from May 26 to May 27
￥20,994
￥24,959 total
May 26 - May 27
includes taxes & fees
8/10 Very Good! (10,220 reviews)
The bar being open late is nice and the staff are very helpful.

Reviewed on May 12, 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 ￥23,481 per night from May 25 to May 26
￥23,481
￥32,406 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,127 reviews)
Very clean and spacious! Friendly staff Generous breakfast tho coffee could be much better ditto tea…both like dishwater if British take t-bags! If coffee fan have elsewhere. And no water in rooms after first night. Apart from those niggles beds very comfy enjoyable stay…roof top bar a must!

Reviewed on May 12, 2026

Hotel Riu Plaza Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
The price is ￥23,555 per night from May 25 to May 26
￥23,555
￥28,006 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (4,285 reviews)
Valet and bellmen were great as always. Polite and helpful. The staff brought up an extra valet for my kids on the pullout couch. Great setup for family with kids! And the restaurant on the corner has the best coffee. We stay here every time we visit, can’t beat location, price and separate space ...

Reviewed on May 13, 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,679 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 ￥354,982. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.