Skokie Vacations from ￥299,844

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The Latest Skokie Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
Price was ￥350,558, price is now ￥299,844 per person
￥299,844
per person
Jan 11 - Jan 18
found 9 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (1,106 reviews)
Loved it ! One of the most nicest hotels I been to in a long time . I will be back and will recommend! Breakfast was amazing! Room was cozy and most of all clean !

Reviewed on Nov 9, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥440,564, price is now ￥343,515 per person
￥343,515
per person
Dec 24 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
Price to high for the quality.

Reviewed on Nov 9, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥405,868, price is now ￥332,054 per person
￥332,054
per person
Dec 24 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,962 reviews)

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was ￥397,070, price is now ￥331,151 per person
￥331,151
per person
Dec 24 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,572 reviews)

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was ￥396,881, price is now ￥331,043 per person
￥331,043
per person
Dec 24 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
I was surprised by the $29.50 daily charge for "Guest Amenity Fee". I did not ask for it. I don't even know what it is. I hate when hotels charge you hidden items.

Reviewed on Nov 9, 2026

Find the Best Skokie Vacation Packages

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 ￥18,345 per night from Nov 23 to Nov 24
￥18,345
￥21,812 total
Nov 23 - Nov 24
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 ￥18,324 per night from Nov 23 to Nov 24
￥18,324
￥21,788 total
Nov 23 - Nov 24
includes taxes & fees
8/10 Very Good! (2,695 reviews)
"Love this hotel! It was really nice, staff were very friendly and helpful! Restaurant and bar were perfect and open late. Paid breakfast buffet was nice as well!"

Reviewed on Nov 10, 2026

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 ￥16,799 per night from Dec 10 to Dec 11
￥16,799
￥19,971 total
Dec 10 - Dec 11
includes taxes & fees
River Hotel
See all 4,723 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.

Stay near popular Skokie attractions

North Shore Center for the Performing Arts

8.0/10 (61 reviews)
This intimate cultural venue houses two theaters showcasing diverse performances. Enjoy excellent acoustics and sightlines before exploring nearby dining options for a complete evening experience.
See properties

What to do in Skokie

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥3,809
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

￥6,269
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

￥6,636
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
See all activities in Skokie

Frequently asked questions

How much does a Skokie vacation package cost?
Offering excellent value package deals from ￥299,844 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.