Sheffield and DePaul Vacation Packages

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Top Holiday Package Deals in Sheffield and DePaul

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,209, price is now CA $912 per person
CA $912
per person
Oct 23 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,038 reviews)
This was the best hotel I’ve stayed in in my life. I came here for the first time to Chicago and me and my girl. Upon arrival they gave us a complementary room upgrade. Where are they doing that at so as you can see, I am very happy with our stay so I will recommend this hotel to anybody and I think we might even come back here again. You know any they have good amenities

Reviewed on Jul 30, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,854, price is now CA $1,286 per person
CA $1,286
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (540 reviews)
Comes with all the comforts of Home.

Reviewed on Jul 29, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,391, price is now CA $1,023 per person
CA $1,023
per person
Sep 4 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (509 reviews)

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was CA $3,399, price is now CA $2,537 per person
CA $2,537
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
My friend and I stayed for her bachelorette day celebration, it was both of our first time at The Langham. We both loved our stay and would absolutely return in the future. I've stayed in many hotels and the staff here really take it to another level, and in a way that feels genuine. Some hotels really know how to hire people who sincerely want to help others create special moments, and we really felt that at The Langham. It is hard to really enjoy this place in one day, but that just means we'll have to return soon! Thank you, Langham Staff.

Reviewed on Jul 29, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,492, price is now CA $1,118 per person
CA $1,118
per person
Sep 9 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,144 reviews)
Wonderful stay. O

Reviewed on Jul 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
A busy city street with tall buildings, a bus, and cars.

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 CA $199 per night from Aug 30 to Aug 31
CA $199
CA $237 total
Aug 30 - Aug 31
includes taxes & fees
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 CA $213 per night from Aug 16 to Aug 17
CA $213
CA $253 total
Aug 16 - Aug 17
includes taxes & fees
8/10 Very good! (1,876 reviews)
"Amazing hotel! Central location and awesome place to stay in the city!"

Reviewed on Jul 31, 2026

The Chicago Hotel Collection Ambassador Gold Coast
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 CA $237 per night from Aug 30 to Aug 31
CA $237
CA $270 total
Aug 30 - Aug 31
includes taxes & fees
Hyatt Regency O'Hare Chicago
See all 4,492 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.
All Inclusive Vacations
All Inclusive Vacations
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Frequently asked questions

How much does a Sheffield and DePaul vacation package cost?
From as low as CA $912. 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 entertainment choices.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $64
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
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.