Skokie Vacations from $193

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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.

The Latest Skokie vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
The Westin Michigan Avenue Chicago
Hilton Grand Vacations Club Chicago Magnificent Mile
The French Country Inn Lake Geneva
Level Chicago - River North
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Discover the most popular places to visit in Skokie

What to do in Skokie

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
$145 nightly
The price is $170 total per night from Nov 2 to Nov 3
$170 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (9,331 reviews)
"Very clean"

Reviewed on Oct 7, 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $118 total per night from Nov 4 to Nov 5
$118 total
Nov 4 - Nov 5
Total with taxes and fees
7.8/10 Good! (2,419 reviews)
Great stay
"This weekend was a full house but even with there being so many people for the dorm rooms the staff still tried to accommodate as much as possible."

Reviewed on Oct 5, 2025

Freehand 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
$169 nightly
The price is $199 total per night from Nov 5 to Nov 6
$199 total
Nov 5 - Nov 6
Total with taxes and fees
8.4/10 Very Good! (5,051 reviews)
"Wonderful place, great staff, delicious breakfast and happy hour"

Reviewed on Oct 6, 2025

Embassy Suites by Hilton Chicago Downtown River North
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.

Skokie Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
64,800
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Chicago Riverwalk, Art Institute of Chicago and Chicago Theatre

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Frequently asked questions

How much does a Skokie vacation package cost?
Offering excellent value package deals from $193 on Expedia, you'll be surprised at how little a vacation to Skokie costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Skokie?
If you'd like to snag a cheap Skokie vacation package, consider visiting in December, January and February. You'll generally find better prices on airfares and hotels during these quieter months — ideal for a budget-friendly break.
How many days is enough for Skokie?
To fully enjoy your Skokie vacation, we recommend staying for 2 days. Divide your time between discovering Emily Oaks Nature Center, Schaefer's Wines and Liquors and other key sights, as well as experiencing neighborhoods like O'Hare and Norwood Park. If you've got some time to spare, include a day trip in your Skokie vacation itinerary.
Is it worth booking a vacation package to Skokie?
Boasting a host of highlights starting with its excellent history, Skokie is a good vacation destination. Whether you'd like to visit sights like North Shore Center for the Performing Arts and Skokie Theatre or take the path less traveled, you'll find loads to see and do on your Skokie vacation.
How to find the best Skokie package deals?
Start your search for a Skokie package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Skokie package deal right away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Skokie escape off to a flying start.
Is it cheaper to book a Skokie vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component individually. And you'll still get the freedom to create a customized Skokie vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Skokie?
If you're considering an impromptu Skokie trip, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Skokie?

  1. Choose when to travel: Check your calendar and get packing. Your favorite time of year and the type of activities available will also help you decide when to visit Skokie.
  2. Set your budget: Factor in costs such as flights, meals and transportation when calculating how much to set aside for your trip to Skokie. Then, pick a hotel that suits your budget, whether that's a wallet-friendly stay or a more upscale retreat.
  3. Discover Skokie with Expedia's trip planning tool: Gain insights into the leading attractions and best properties for your trip to Skokie. You can also save your favorite locations, collaborate with family and friends and arrange all your plans in one place.
  4. Decide how long to go away for: Now that you're more familiar with Skokie, you can work out the ideal length of your break. Pull together a rough itinerary and give yourself enough time to cover everything you want to see.
  5. Combine your airfare and accommodations: After you've nailed down your trip dates and duration, book the right Skokie vacation package for you.
  6. Add on experiences and excursions: Take a look at our dedicated travel guide to find some awesome things to do in Skokie. Book tickets or make reservations as soon as you can to save time and skip the hassle of looking for activities when you arrive.

Does Expedia offer Book Now, Pay Later Skokie vacation packages?
If you're anything like us, you love going away but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Skokie break over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you see them.

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Explore a world of travel with Expedia

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