Stephenson County Vacation Packages

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  • Better together

    Save up to CA $1,096 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

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Top Stephenson County Vacation Deals

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 CA $1,289, price is now CA $978 per person
CA $978
per person
May 8 - May 11
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
The rooms are extremely clean and have everything you need. The staff is so accommodating and friendly. The view is amazing

Reviewed on Mar 27, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,927, price is now CA $1,298 per person
CA $1,298
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Great location. Clean, comfortable, friendly staff.

Reviewed on Mar 30, 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 $1,444, price is now CA $1,054 per person
CA $1,054
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Amazing experience will be back soon

Reviewed on Mar 29, 2026

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,013, price is now CA $1,546 per person
CA $1,546
per person
May 26 - May 30
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,187 reviews)
Very nice place on the Gold Coast!

Reviewed on Mar 23, 2026

Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
Downtown Chicago
Price was CA $1,422, price is now CA $1,094 per person
CA $1,094
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (3,039 reviews)
Requested additional towels, never came. Luggage racks were difficult to obtain. Rooms are small. Bring your own hairdryer. Water pressure in shower is minimal.

Reviewed on Mar 27, 2026

Stephenson County Hotel Deals

Country Inn & Suites by Radisson, Freeport, IL

Country Inn & Suites by Radisson, Freeport, IL

2.5 out of 5
1710 South Dirck Drive Freeport IL
Fully refundable
The price is CA $158 per night from Apr 5 to Apr 6
CA $158
CA $175 total
Apr 5 - Apr 6
includes taxes & fees
9/10 Wonderful! (875 reviews)
The room had only sheers covering the window. No privacy at night. There was also a bright light shining up to show the building that made it impossible to have a dark room (even with a blanket drapes across it!). The walls are thin (I could hear the room next door snoring). The internet connection ...

Reviewed on Mar 22, 2026

Country Inn & Suites by Radisson, Freeport, IL
Hampton Inn Freeport

Hampton Inn Freeport

2.5 out of 5
109 S Galena Ave Freeport IL
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Apr 6 to Apr 7
CA $147
CA $163 total
Apr 6 - Apr 7
includes taxes & fees
8.8/10 Excellent! (461 reviews)
The breakfast was excellent. The place was clean. And the staff was very helpful.

Reviewed on Mar 30, 2026

Hampton Inn Freeport
Super 8 by Wyndham Freeport

Super 8 by Wyndham Freeport

2 out of 5
1551 Sleezer Home Rd Freeport IL
Fully refundableReserve now, pay when you stay
The price is CA $100 per night from Apr 5 to Apr 6
CA $100
CA $111 total
Apr 5 - Apr 6
includes taxes & fees
6.8/10 (351 reviews)
The proerty manager had several rooms on the 2nd floor with unsupervised kids in it who ran in and out of the rooms banging the doors as they ran through the halls, playing.

Reviewed on Mar 15, 2026

Super 8 by Wyndham Freeport
See all 264 properties in Stephenson County
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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Frequently asked questions

How much does a Stephenson County vacation package cost?
Perhaps much less than you think — from a low CA $978, as a matter of fact! By bundling hotels, flights and car rentals into a custom-built vacation package, your Stephenson County escape is just clicks away.
How do I get a cheap travel package to Stephenson County?
Browse and lock in everything in the one place with our Stephenson County vacation packages. We have incredible bargains on flights, hotels, tours and more that'll keep your credit card happy and your adventurous spirit alive. And, with more than 550 partner airlines and 1,000,000 hotels around the world to choose from, you'll have the flexibility to mix and match as you please.
How far in advance should I book my Stephenson County vacation?
It depends on the airline, but you can generally look up international fares on Expedia nearly a year in advance. While it's a good idea to book ahead of time, lucky customers occasionally score a cheaper seat just weeks prior to their intended journey.
What does an Expedia Stephenson County travel package include?
Flights, hotels and car rentals — we connect you to the very best bargains. All you'll have to do is decide on your ideal combination. After you've made your booking, you can add on the exciting stuff like activities and tours. Our travel packages make it easy to put together an exciting Stephenson County escape.
What should I know before booking a Stephenson County travel package?
Whether it's relaxation or adventure you're seeking, a Stephenson County vacation package lets you organize your escape your way. Plus, you'll get access to great discounts just for combining your accommodations with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Stephenson County Expedia vacation package?
Yes, you're in charge. We offer more than 550 airlines worldwide, so you can design your Stephenson County vacation according to your needs and budget.
If I'm not able to travel, can I cancel my Stephenson County vacation package?
Don't worry if you're rethinking your Stephenson County vacation package — it's possible to cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We know your circumstances can change suddenly, so head to our Customer Service Portal if that happens. When you're ready to make changes, we'll be here to help.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.