Sheffield and DePaul Vacations from ￥278,554

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The Latest Sheffield and DePaul Vacation Packages

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

Arlo Chicago

4 out of 5
Downtown Chicago
Price was ￥340,540, price is now ￥278,554 per person
￥278,554
per person
May 2 - May 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,862 reviews)
Clean room, great location, friendly staff

Reviewed on Feb 12, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥402,916, price is now ￥287,806 per person
￥287,806
per person
May 2 - May 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Rooms were great and breakfast was delicious

Reviewed on Feb 14, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥474,585, price is now ￥358,300 per person
￥358,300
per person
Mar 16 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.

Reviewed on Feb 3, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was ￥360,848, price is now ￥290,400 per person
￥290,400
per person
May 2 - May 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Room was very cold and drafty. On arrival the reception tried to charge us more for the room, for a “city view” which was what we had selected on Expedia when booking. The rooftop bar, in the winter is not open and the indoor bar has no view. The cocktail bar in the lobby is lovely and the service was excellent. Breakfast is available in Land&Lake on the ground floor. And is good. You can also get a To-Go coffee from them.

Reviewed on Feb 14, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was ￥361,603, price is now ￥294,691 per person
￥294,691
per person
Mar 16 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.

Reviewed on Jan 31, 2026

Where to stay in Sheffield and DePaul

Find the best Sheffield and DePaul areas and neighborhoods for the activities you enjoy most. Learn more about Sheffield and DePaul
Downtown Chicago showing 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

Sheffield and DePaul 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 ￥13,628 per night from Feb 16 to Feb 17
￥13,628
￥15,998 total
Feb 16 - Feb 17
includes taxes & fees
8/10 Very Good! (9,880 reviews)
Great location, beautiful historic hotel with clean, updated rooms.

Reviewed on Feb 11, 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 ￥17,250 per night from Feb 16 to Feb 17
￥17,250
￥24,555 total
Feb 16 - Feb 17
includes taxes & fees
9.2/10 Wonderful! (3,341 reviews)
Rooms were great and breakfast was delicious

Reviewed on Feb 14, 2026

Hotel Riu Plaza Chicago
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥29,926 per night from Mar 7 to Mar 8
￥29,926
￥35,130 total
Mar 7 - Mar 8
includes taxes & fees
8.2/10 Very Good! (2,202 reviews)
Food at sports bar was great along with the service. Bedding was top notch, room clean& nice TV

Reviewed on Feb 9, 2026

Hilton Chicago O'Hare Airport
See all 4,743 properties in Sheffield and DePaul
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 Sheffield and DePaul vacation package cost?
From as low as ￥278,554. Yes, you read that right. Our Sheffield and DePaul vacation packages are the quickest way to make your budget go further. Combine your favorite hotels, flights and rental car and explore this destination your way.
How do I get a cheap travel package to Sheffield and DePaul?
If you love getting an amazing deal, bundle your bookings into a Sheffield and DePaul vacation package. Whether you're chasing flights, hotels, rental cars or tours, you can browse and book everything in one place. You'll have plenty of choice at your fingertips too. Expedia has more than 550 partner airlines and 1,000,000 properties around the globe to choose from. Fly with who you want, stay where you like and save precious dollars — now that's the perfect vacation!
Where should I stay in Sheffield and DePaul?
Take the leg work out of sightseeing by staying in a hotel within walking distance of Sheffield and DePaul's terrific attractions. Wrigley Field and Lincoln Park Zoo are two of the best in this neighborhood.
What are the top hotels in Sheffield and DePaul?
When it comes to comfy and convenient places to stay in Sheffield and DePaul, you can't go past Villa D' Citta. Be sure to browse its deals and pick up a bargain.
How far in advance should I book my Sheffield and DePaul vacation?
Reserving your tickets early with Expedia means one less thing to worry about. Most carriers advertise tickets up to 12 months in advance. Usually, this is the cheapest time to book. If circumstances have left you booking late, great deals to Sheffield and DePaul occasionally appear a few weeks before departure.
What does an Expedia Sheffield and DePaul travel package include?
Packages include flights, hotels and rental cars, but you can combine any of them to create your ideal Sheffield and DePaul getaway. You can also add on a few activities and tours once you've made your booking. You're the boss! When you bundle your bookings with Expedia, you'll score deals you won't find anywhere else.
What should I know before booking a Sheffield and DePaul travel package?
A package can be easier on the credit card than separately booking all you need for your adventure. For example, bundle your hotels, flights and rental cars and land a great deal. No matter your vacation goals, you're sure to find a package that matches your budget.
Can I choose my airline with a Sheffield and DePaul Expedia vacation package?
Yes, the choice is all yours. Expedia has access to more than 550 partner airlines throughout the world, so you can customize your Sheffield and DePaul escape according to your style and budget.
If I'm not able to travel, can I cancel my Sheffield and DePaul vacation package?
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 Sheffield and DePaul vacation package. It may be possible to cancel or amend your itinerary at no cost if you've booked within 24 hours. Your airline, hotel or car rental company may impose a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for more information. Also, be sure to check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Sheffield and DePaul

Blues on Halstead

You can make plans for a show at Blues on Halstead during your trip to Chicago. Experience the entertainment choices and acclaimed art scene in this vibrant area.

Blues on Halstead

Things to do

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,883
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥6,269
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Art Institute of Chicago

Art Institute of Chicago

￥6,325
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.