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.
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
Downtown Chicago
per person
Jul. 4 - Jul. 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,064 reviews)
Easy accessible to all Chicago has to offer

Reviewed on Apr. 30, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 10 - Jul. 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,605 reviews)
Love the rooftop! You get a beautiful view of the city.

Reviewed on Apr. 30, 2025

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
per person
Jul. 4 - Jul. 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Great property in Chicago. Quiet rooms

Reviewed on Apr. 28, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 5 - Jun. 9
found 18 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9/10 Wonderful! (295 reviews)
The staff wasn’t very welcoming. After booking, they send you a form asking for almost everything except your social security number. I understand it’s for the safety of the residents, but I didn’t feel comfortable providing that much information. It felt like I had no choice but to go through with it since I wouldn’t get my money back otherwise. The walls are also extremely thin; you can hear everything. One of the neighbors blasted music from 6 PM until 1 AM on a Tuesday. They only turned it down after I reported it. Overall, I wouldn’t stay here again.

Reviewed on Apr. 30, 2025

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
per person
Jul. 4 - Jul. 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,444 reviews)
The hotel clerk who welcomed us upon checking in was the most gracious!

Reviewed on Apr. 24, 2025

Ready to book your vacation to Skokie?

 

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Skokie Hotel Deals

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 $228 per night from May 1 to May 2
CA $228
CA $268 total
includes taxes & fees
May 1 - May 2
8.2/10 Very Good! (3,960 reviews)
"Very smooth check in, we had a great stay. Very helpful at the front not only at check in but with directions and help throughout the stay."

Reviewed on Apr. 29, 2025

Embassy Suites by Hilton Chicago Downtown River North
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 $165 per night from May 27 to May 28
CA $165
CA $193 total
includes taxes & fees
May 27 - May 28
7.8/10 Good! (8,715 reviews)
"Really nice hotel next to millennium park."

Reviewed on Apr. 28, 2025

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $222 per night from May 8 to May 9
CA $222
CA $261 total
includes taxes & fees
May 8 - May 9
8.8/10 Excellent! (2,164 reviews)
"Pool and fitness center was not in service."

Reviewed on Apr. 28, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,407 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Skokie vacation package cost?
You can pick up a vacation package to this top destination from CA $606 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.

Discover the most popular places to visit in Skokie

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Six Flags Great America featuring rides

Six Flags Great America

4.5/5(5 reviews)

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

4.5/5(19 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue

What to do in Skokie

Flyover in Chicago

Flyover in Chicago

CA $53
per adult
98% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

CA $67
per adult
94% of travellers recommend
Architecture River Tour
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

CA $62
per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
See all activities in Skokie
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.