Skokie Vacations

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Find the Best Skokie Vacation Packages

Skokie Hotel Deals

Holiday Inn Chicago North Shore by IHG

Holiday Inn Chicago North Shore by IHG

3 out of 5
5300 West Touhy Ave, Skokie, IL
Fully refundable
The price is NT$3,424 per night from Sep 1 to Sep 2
NT$3,424
NT$3,920 total
Sep 1 - Sep 2
includes taxes & fees
7.4/10 Good! (1,340 reviews)
"Excellent"

Reviewed on 2025/8/18

Holiday Inn Chicago North Shore by IHG
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NT$4,616 per night from Sep 1 to Sep 2
NT$4,616
NT$5,419 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,211 reviews)
"The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude ..."

Reviewed on 2025/8/20

The Wade
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 NT$5,751 per night from Sep 14 to Sep 15
NT$5,751
NT$6,751 total
Sep 14 - Sep 15
includes taxes & fees
7.8/10 Good! (8,996 reviews)
Great view! Safe location for food music and park
"Got a very good rate during an event that had filled up many nearby hotels. Lovely sparkling-clean room, rather small, a firm king bed, dresser, & table. It felt cozy, not crowded, enough drawers and closet space, nice-size bathroom with shower-tub. Room has nice ornate details. 10th-floor sunrise ..."

Reviewed on 2025/8/24

Congress Plaza Hotel
See all 4,872 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.

Discover the most popular places to visit in Skokie

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

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

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

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
Navy Pier featuring a sunset and rides

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Frequently asked questions

How much does a Skokie vacation package cost?
Offering excellent value package deals 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're looking to snag a cheap Skokie vacation package, consider planning a trip in January, February and November. You'll usually find better rates on hotels and airfares during these quieter months — ideal for travelers wishing to save money.
How many days is enough for Skokie?
To fully enjoy a Skokie vacation, we recommend staying for 2 days. Split your time between visiting Emily Oaks Nature Center, Schaefer's Wines and Liquors and other key sights, in addition to experiencing neighborhoods like O'Hare and Norwood Park. If you've got some time to spare, add a day trip or tour to your Skokie vacation itinerary.
Is it worth booking a vacation package to Skokie?
Well known for its history and home to leading attractions like North Shore Center for the Performing Arts, a Skokie vacation is sure to impress. Another top sight to visit? Don't miss Skokie Theatre.
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. Pick your dates: What you'd like to do in Skokie and your preferred season can help you decide when to go.
  2. Calculate your budget: Make sure you have enough money to cover everything from transportation and food to experiences and flights. Your hotel will likely be the biggest expense during your trip to Skokie.
  3. Decide how many days away: Start by compiling a list of the sights and activities you want to get to in Skokie. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to choose a Skokie vacation package that brings all your bookings together.

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