Skokie Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AEDĀ 5,000 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

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 AEDĀ 529 per night from Jul 27 to Jul 28
AEDĀ 529
AEDĀ 628 total
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very Good! (1,720 reviews)
"Great time"

Reviewed on 9 July 2026

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 AEDĀ 790 per night from Aug 9 to Aug 10
AEDĀ 790
AEDĀ 1,062 total
9 Aug - 10 Aug
includes taxes & fees
9.2/10 Wonderful! (1,886 reviews)
"The room was amazing! It was spacious and clean. The staff were helpful and very considerate. The hotel is located in an ideal location, right off of Michigan Avenue, in the heart of downtown. Shopping and restaurants are within short walking distances."

Reviewed on 8 July 2026

Omni Chicago Hotel
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 AEDĀ 681 per night from Aug 6 to Aug 7
AEDĀ 681
AEDĀ 810 total
6 Aug - 7 Aug
includes taxes & fees
8/10 Very Good! (10,209 reviews)
"I was freezing and they were super gracious and got me TWO blankets."

Reviewed on 9 July 2026

Congress Plaza Hotel
See all 4,679 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.