Skokie Holidays

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Top Flight + Hotel Deals in Skokie

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Great area: able to walk to many restaurants.

Reviewed on 18 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
Rooms are basic and bathrooms and sink area small. But all comfortable

Reviewed on 17 Aug 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,008 reviews)
Great! Just watch out for the additional fees when checking out.

Reviewed on 18 Aug 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (335 reviews)
Great property. Outstanding all the way around.

Reviewed on 13 Aug 2025

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very Good! (1,829 reviews)
It’s a beautiful hotel with lovely staff. The beds were very comfy but the pillows have no neck support. We loved how close it was to Millennium park and how walkable the area was for finding dining options and seeing the sights. It’s only about one city block from the Art Institute and we got to walk by those beautiful lions every day. We did not try the restaurant but did have a drink at the Lockwood bar. The drinks were well balanced but it took forever to get drinks; I had to wait 15 minutes just to place my order at the bar with three bartenders. We didn’t see any waiters to help either.

Reviewed on 18 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 €189 per night from 14 Sept to 15 Sept
€189
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (8,938 reviews)
"Friendly staff, clean rooms, huge hotel. Good location"

Reviewed on 16 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! (1,189 reviews)
"Nice location near the pier"

Reviewed on 17 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

4.5/5(40 reviews)

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

4.5/5(14 reviews)

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

4/5(125 reviews)

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 €625 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.