Skokie Holidays

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Top Flight + Hotel Deals in Skokie

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was €1,169, price is now €779 per person
€779
per person
2 Nov - 7 Nov
found 2 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,008 reviews)
The service was excellent, they made my birthday very special!

Reviewed on 19 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €1,927, price is now €1,160 per person
€1,160
per person
2 Nov - 7 Nov
found 2 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was €1,782, price is now €1,218 per person
€1,218
per person
2 Nov - 7 Nov
found 2 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on 12 Aug 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was €1,282, price is now €879 per person
€879
per person
2 Nov - 7 Nov
found 2 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
One of the tvs didnt work, and neither did the room phone. Dislike the texting communication, and having to go thru 3rd party just to call front desk.

Reviewed on 17 Aug 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was €2,287, price is now €1,575 per person
€1,575
per person
2 Nov - 7 Nov
just found
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
The most beautiful hotel !

Reviewed on 17 Aug 2025

Top hotels in Skokie

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 €110 per night from 1 Sept to 2 Sept
€110
1 Sept - 2 Sept
includes taxes & fees
7.4/10 Good! (1,340 reviews)
"Easy navigation and able to walk to get late night eats. Staff was super friendly"

Reviewed on 17 Aug 2025

Holiday Inn Chicago North Shore by IHG
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is €190 per night from 14 Sept to 15 Sept
€190
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (9,006 reviews)
"Great history . Staff was excellent"

Reviewed on 19 Aug 2025

Congress Plaza Hotel
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 €152 per night from 1 Sept to 2 Sept
€152
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,205 reviews)
"The pool could have been a bit better"

Reviewed on 19 Aug 2025

The Wade
See all 4,853 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.

Popular places to visit

Wrigley Field featuring central business district, a city and a sporting event

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 street scenes, signage and night scenes

Michigan Avenue

You can find the perfect gifts to bring home 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

Navy Pier

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

Navy Pier

What to do in Skokie

River tour boat in Chicago

Architecture River Tour

€36
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

€39
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

€35
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Skokie

Frequently asked questions

How much does a Skokie holiday package cost?
Offering excellent value package deals from €779 on Expedia, you'll be surprised at how little a holiday 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 holiday 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 travellers wishing to save money.
How many days is enough for Skokie?
To fully enjoy a Skokie holiday, we recommend staying for 2 days. Split your time between visiting Emily Oaks Nature Centre, Schaefer's Wines and Liquors and other key sights, in addition to experiencing neighbourhoods like O'Hare and Norwood Park. If you've got some time to spare, add a day trip or tour to your Skokie holiday itinerary.
Is it worth booking a holiday package to Skokie?
Well known for its history and home to leading attractions like North Shore Centre for the Performing Arts, a Skokie holiday 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 holiday as a package?
Expedia holiday 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 customised Skokie holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday 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 holiday 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.