Skokie Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Skokie Vacation Packages

Skokie Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is SARĀ 635 per night from Aug 3 to Aug 4
SARĀ 635
SARĀ 723 total
3 Aug - 4 Aug
includes taxes & fees
8.8/10 Excellent! (2,840 reviews)
"Everything was good"

Reviewed on 17 July 2026

Hyatt Regency O'Hare Chicago
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 SARĀ 728 per night from Jul 19 to Jul 20
SARĀ 728
SARĀ 866 total
19 Jul - 20 Jul
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is SARĀ 1,003 per night from Jul 26 to Jul 27
SARĀ 1,003
SARĀ 1,317 total
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (1,924 reviews)
"Fantastic!"

Reviewed on 17 July 2026

Omni Chicago Hotel
See all 4,673 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

Skokie Theatre

8.2/10 (59 reviews)
This intimate Art Deco theater captivates with diverse live performances in a historic setting. Reserve tickets early for popular shows to experience exceptional acoustics and perfect sight lines from every seat.
See properties

Frequently asked questions

How much does a Skokie vacation package cost?
You can pick up a vacation package to this top destination 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 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 favorite 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 favorite 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.