Douglas Vacations from ￥285,602

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥45,448 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

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Douglas Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥335,334, price is now ￥285,602 per person
￥285,602
per person
May 14 - May 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Elegant and beautiful

Reviewed on Mar 26, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥546,288, price is now ￥399,292 per person
￥399,292
per person
Apr 29 - May 5
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
This is the best hotel I’ve been so far, their staffs were supper nice and their rooms are amazing, thanks

Reviewed on Mar 28, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was ￥374,696, price is now ￥314,217 per person
￥314,217
per person
Jun 11 - Jun 14
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Staff were awesome!! Room view was amazing . Only complaint if I had one would be we didn’t get our room turned over one of the days.

Reviewed on Mar 28, 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥446,148, price is now ￥381,583 per person
￥381,583
per person
Apr 29 - May 5
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.4/10 Very Good! (1,862 reviews)
This was perfect for a night in the city! Great all around and will stay again. Great staff at check-in!

Reviewed on Mar 27, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥443,372, price is now ￥382,310 per person
￥382,310
per person
Apr 29 - May 5
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Christian was a wonderful help.

Reviewed on Mar 27, 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
Fully refundableReserve now, pay when you stay
The price is ￥18,396 per night from Apr 5 to Apr 6
￥18,396
￥21,596 total
Apr 5 - Apr 6
includes taxes & fees
8/10 Very Good! (9,996 reviews)
Small rooms

Reviewed on Mar 28, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥21,975 per night from Apr 5 to Apr 6
￥21,975
￥25,796 total
Apr 5 - Apr 6
includes taxes & fees
9/10 Wonderful! (3,995 reviews)
We stayed 5 days our room was cleaned each day! We had a great stay!

Reviewed on Mar 28, 2026

Hilton Chicago/Magnificent Mile Suites
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
Fully refundableReserve now, pay when you stay
The price is ￥23,303 per night from Apr 12 to Apr 13
￥23,303
￥27,355 total
Apr 12 - Apr 13
includes taxes & fees
8.6/10 Excellent! (5,786 reviews)
The staff was very friendly and helpful.

Reviewed on Mar 27, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,650 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 ￥285,602. 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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥3,985
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,829
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

￥6,236
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.