Sheffield and DePaul Vacations from ￥292,083

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The Latest Sheffield and DePaul Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ￥350,859, price is now ￥292,083 per person
￥292,083
per person
Aug 17 - Aug 21
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (484 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.

Reviewed on Jun 11, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was ￥357,804, price is now ￥293,862 per person
￥293,862
per person
Aug 17 - Aug 21
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (491 reviews)
If you drive, it’s very close to everything pretty much. It’s clean and nice to stay with family. Parking is a little expensive but that applies to most of Chicago area.

Reviewed on Jun 14, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was ￥369,264, price is now ￥305,394 per person
￥305,394
per person
Aug 17 - Aug 21
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,325 reviews)
Rooftop Movie theater looked fun during the daytime, but wasn’t committed enough to buy a ticket after sunset. Rooms were fine. Coffee shop was short-staffed the day I was there - to the point I gave up and moved on. The staff I ran into in the hotel from housekeeping to front desk to bell staff were all universally pleasant and helpful. Location was great - convenient to the show I was attending at the Cobra Lounge and to a pretty decent variety of decent looking food options. Don’t miss the Hubbard St viaducts on your morning walk.

Reviewed on Jun 8, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥443,444, price is now ￥366,781 per person
￥366,781
per person
Aug 17 - Aug 21
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,888 reviews)
The fitness center & spa was top notch. The on site restaurant had amazing food and service.

Reviewed on Jun 12, 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was ￥444,968, price is now ￥369,419 per person
￥369,419
per person
Aug 17 - Aug 21
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,376 reviews)
We had requested for a 2pm checking but they gave us the room at 4pm and the normal checkin time is 3pm. Also the next day they did nit clean the room and we had requested that the beds and bathroom needs to be cleaned. They cleaned the room but left. Soaking wet towel on the bed. Little disappointed with our stay.

Reviewed on Jun 7, 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

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

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 ￥21,786 per night from Jun 29 to Jun 30
￥21,786
￥25,901 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,264 reviews)
"Great stay!"

Reviewed on Jun 14, 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is ￥23,131 per night from Jun 30 to Jul 1
￥23,131
￥27,501 total
Jun 30 - Jul 1
includes taxes & fees
7.8/10 Good! (1,579 reviews)
"The hotel was a great location and very clean and and staff was nice and friendly!"

Reviewed on Jun 14, 2026

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is ￥25,478 per night from Jun 28 to Jun 29
￥25,478
￥29,041 total
Jun 28 - Jun 29
includes taxes & fees
8.8/10 Excellent! (2,666 reviews)
"Overall stay was great with my brother. I will come back agin. Staff were helpful especially with our shuttle ride to the airport."

Reviewed on Jun 13, 2026

Hyatt Regency O'Hare Chicago
See all 4,584 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 ￥292,083. 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.

Stay near popular Sheffield and DePaul attractions

Lincoln Hall

You can enjoy a show at Lincoln Hall during your stay in Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.