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.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $984, price is now CA $740 per person
CA $740
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,050, price is now CA $776 per person
CA $776
per person
Dec 4 - Dec 6
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,127 reviews)

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,154, price is now CA $879 per person
CA $879
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)
The stay was everything I love the view and peaceful. Thank you

Reviewed on Oct 26, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $981, price is now CA $759 per person
CA $759
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very good! (3,148 reviews)
Location was great. Front desk staff were friendly and helpful

Reviewed on Oct 26, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,877, price is now CA $1,456 per person
CA $1,456
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
The best of the best. The largest rooms in town at the very best price with the very best experience.

Reviewed on Oct 26, 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 $146 per night from Nov 22 to Nov 23
CA $146
CA $174 total
Nov 22 - Nov 23
includes taxes & fees
8/10 Very good! (10,118 reviews)
"The rooms were really small and it could use some updating for sure however it did have a vintage feel and really nice restaurant and bar with very nice staff. Parking was expensive and on a different block which was inconvenient"

Reviewed on Oct 27, 2026

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 $170 per night from Nov 22 to Nov 23
CA $170
CA $203 total
Nov 22 - Nov 23
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Nov 25 to Nov 26
CA $162
CA $193 total
Nov 25 - Nov 26
includes taxes & fees
8.8/10 Excellent! (5,575 reviews)
"Not the greatest property, outdated"

Reviewed on Oct 26, 2026

River Hotel
See all 4,909 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

North Shore Center for the Performing Arts

8.0/10 (61 reviews)
Enjoy a stop at North Shore Center for the Performing Arts, an entertaining place to visit in Skokie. Experience the great live music 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 $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

CA $57
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $60
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
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 $740 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.