Skokie Vacation Packages

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Your Skokie Vacation

There's no better way to escape than with one of our vacation packages to Skokie. The diversity and progressive thinking are a couple of the compelling reasons you'll want to stay in this awesome city. Like to get out and explore? Northwestern University, Loyola University Chicago and Aragon Ballroom are three of the leading places to visit during your trip to Skokie. Your ideal Skokie vacation is a couple of clicks away. Search hotels, airfares and more on Expedia for a getaway that's tailored to suit your style.

Top Skokie Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,991, price is now CA $1,339 per person
CA $1,339
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,854 reviews)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $3,188, price is now CA $1,847 per person
CA $1,847
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)
Nice area

Reviewed on Jul 28, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $3,257, price is now CA $2,088 per person
CA $2,088
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (533 reviews)

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $2,776, price is now CA $1,853 per person
CA $1,853
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,038 reviews)
Loved it

Reviewed on Jul 28, 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 $2,283, price is now CA $1,568 per person
CA $1,568
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,606 reviews)
Hotel and staff were friendly and inviting, the room itself was beautifully up-kept and amenities were great except for the charging station. View was absolutely stunning but window could’ve been cleaner to allow for a better experience. Overall had an enjoyable experience at this hotel!

Reviewed on Jul 27, 2026

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Skokie 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 $242 per night from Aug 13 to Aug 14
CA $242
CA $288 total
Aug 13 - Aug 14
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 $253 per night from Aug 9 to Aug 10
CA $253
CA $301 total
Aug 9 - Aug 10
includes taxes & fees
8.2/10 Very good! (1,862 reviews)
"We couldn’t check in til 4 pm. There is NO place to park so we had to"

Reviewed on Jul 27, 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
Get rates
Hyatt Regency O'Hare Chicago
See all 4,751 properties in Skokie
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.
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Stay near popular Skokie attractions

Skokie Theatre

8.2/10 (59 reviews)
You can make plans for a show at Skokie Theatre during your trip to Skokie. Experience the entertainment choices or attend a sporting event in this vibrant area.
See properties

What to do in Skokie

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 Skokie

Frequently asked questions

How much does a Skokie vacation package cost?
You can pick up a vacation package to this top destination from CA $1,339 on Expedia. However, how much your vacation to Skokie costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Skokie?
You're likely to find lower prices and greater availability in January, February and November. Take a look at our cheap Skokie vacation packages and you could land some excellent off-season deals.
How many days is enough for Skokie?
Skokie vacations can be as short or long as you like, but to really sink your teeth into this place, we'd suggest 2 days is about right. In this timeframe, you can visit top sights like Riviera Theatre and Norridge Park District as well as lesser-known spots. Don't skip neighbourhoods such as O'Hare and Norwood Park either. If you're smart with your time, you can even allow for a day trip from Skokie too.
Is it worth booking a vacation package to Skokie?
From top attractions such as North Shore Centre for the Performing Arts and Skokie Theatre to its excellent history, a Skokie vacation delivers big on experiences. With so much to do and see, find out for yourself why Skokie is such a good vacation destination.
How to find the best Skokie package deals?
Use Expedia's filters to help you find some great Skokie package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Skokie package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Skokie vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component separately. And you'll still have the freedom to create a tailored Skokie vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Skokie?
Score fantastic discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Skokie trip.
How to plan a trip to Skokie?

  1. Choose when to get away: Check your schedule and get packing. Your favourite time of year and the type of activities available will also help you decide when to escape to Skokie.
  2. Budget wisely: In addition to the price of your stay, you'll need to consider other expenses. These include transportation, food and flights. Also, set aside a little extra for unexpected costs that may arise during your trip to Skokie.
  3. Decide how long to go away for: Now that you know more about Skokie, you can figure out the ideal length of your vacation. Pull together a rough plan and allocate enough time to cover everything you want to see.
  4. Combine your accommodations and airfare: Once you've nailed down your travel dates and duration, lock in the ideal Skokie vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.