Sheffield and DePaul Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in Sheffield and DePaul

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

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,239, price is now CA $928 per person
CA $928
per person
Apr 23 - Apr 26
found 21 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,007 reviews)
The spa was wonderful, the room was clean and comfortable, and the staff was friendly. I only wish they had more food options. I have allergies and it was difficult to find items

Reviewed on Mar 9, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,878, price is now CA $1,207 per person
CA $1,207
per person
May 18 - May 22
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
Beautiful room. Property upgraded to 2-bedroom. Facilities are great with huge gym. Great stay in Chicago.

Reviewed on Mar 14, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,536, price is now CA $1,063 per person
CA $1,063
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Staff was really nice and polite, Portuguese and Spanish speakers which was a must and breakfast buffet was amazing, highly recommended!

Reviewed on Mar 15, 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 CA $1,456, price is now CA $1,022 per person
CA $1,022
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Great spot and view, would stay again!

Reviewed on Mar 13, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $1,959, price is now CA $1,463 per person
CA $1,463
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
8.6/10 Excellent! (2,076 reviews)
Very nice & clean hotel and near the Bean and shops are walkable.

Reviewed on Mar 3, 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

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 CA $133 per night from Apr 1 to Apr 2
CA $133
CA $156 total
Apr 1 - Apr 2
includes taxes & fees
8/10 Very Good! (9,932 reviews)
We had a lovely stay. The lake view was beautiful and the location was excellent. Staff were friendly and Chris, the bartender, was an amazing historic resource. Thanks for the stay everyone! Ya’ll made our first time in Chicago comforting.

Reviewed on Mar 15, 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 CA $181 per night from Mar 22 to Mar 23
CA $181
CA $251 total
Mar 22 - Mar 23
includes taxes & fees
9.4/10 Exceptional! (3,536 reviews)
Staff was really nice and polite, Portuguese and Spanish speakers which was a must and breakfast buffet was amazing, highly recommended!

Reviewed on Mar 15, 2026

Hotel Riu Plaza Chicago
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 CA $166 per night from Mar 22 to Mar 23
CA $166
CA $195 total
Mar 22 - Mar 23
includes taxes & fees
8.6/10 Excellent! (5,742 reviews)
Just a little loud.

Reviewed on Mar 15, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,706 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
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Beach Vacations
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Frequently asked questions

How much does a Sheffield and DePaul vacation package cost?
From as low as CA $928. 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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $36
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago 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.