Skokie Holidays from £827

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Your Skokie Holiday

There's no better way to escape than with one of our holiday packages to Skokie. The diversity and progressive thinking are a couple of the compelling reasons you'll want to stay in this awesome city. Like to get out and explore? Northwestern University, Loyola University Chicago and Aragon Ballroom are three of the leading places to visit during your trip to Skokie. Your ideal Skokie holiday is a couple of clicks away. Search hotels, airfares and more on Expedia for a getaway that's tailored to suit your style.

Top Skokie Flight + Hotel Deals

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
per person
5 Oct - 8 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9/10 Wonderful! (1,000 reviews)
In my opinion you are paying for the convenience. The location hotel is perfect. You pretty much can walk to shopping centers and stores. The rooftop is awesome but is hard to get into because of outside reservations.

Reviewed on 16 Jul 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
5 Oct - 8 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Excellent stay - outstanding Director of Rooms and valet staff made my daughters wedding an amazing experience - just outstanding !!

Reviewed on 16 Jul 2025

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
8 Oct - 14 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (128 reviews)
Always a great place to stay!

Reviewed on 25 Jun 2025

Art Villa

Art Villa

5 out of 5
West Town
per person
5 Oct - 8 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
No reviews
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
5 Oct - 8 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Superb customer service, clean hotel!

Reviewed on 13 Jun 2025

Skokie Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
64,800
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Chicago Riverwalk, Art Institute of Chicago and Chicago Theatre

Top hotels in Skokie

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 £129 per night from 5 Aug to 6 Aug
£129
5 Aug - 6 Aug
includes taxes & fees
7.8/10 Good! (8,967 reviews)
Great Vacation!
"Loved Chicago and it was close to all the things we wanted to do. Able to walk everywhere and enjoy the water, parks, downtown area, etc."

Reviewed on 14 Jul 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is £217 per night from 10 Aug to 11 Aug
£217
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (2,029 reviews)
"Clean, great location ."

Reviewed on 12 Jul 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £129 per night from 10 Aug to 11 Aug
£129
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (2,452 reviews)
"We had a great time here!"

Reviewed on 15 Jul 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,719 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

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
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
Magnificent Mile - River North which includes 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

What to do in Skokie

River tour boat in Chicago

Architecture River Tour

£36
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£33
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Skokie

Frequently asked questions

How much does a Skokie travel package cost?
Browse and book everything in one place with our Skokie travel packages, which start from only £827. Select the flights and hotels that match your travel style. Then, add on a couple of activities or tours to round off your unique escape.
If I'm not able to travel, can I cancel my Skokie travel package?
It is possible to cancel your Skokie booking if your travel plans have been upended. Whether you'll be charged a fee or not depends on your hotel, airline or car rental company. It may be possible to change or cancel your booking free of charge if you booked in the last 24 hours. Visit our Customer Service Portal for more information.
How do I get a cheap travel package to Skokie?
Browse and book everything in the one place with our Skokie travel packages. You'll discover deals on flights, hotels, tours and more that'll keep your credit card happy and your adventurous spirit full. And, with more than 550 airlines and 1,000,000 hotels throughout the world to select from, there are endless opportunities to mix and match as you like.
Does Expedia offer Book Now, Pay Later Skokie holidays?
We do. Expedia has partnered with online lender Klarna to help you easily pay for your holiday in instalments. Simply select the payment plan that suits you best during checkout and take the stress out of budgeting for your next trip. Make sure you bundle your accommodation, car hire and flights with Expedia to get the biggest bang for your holiday buck. Consider these flexible payment options below:

  • Pay monthly holidays: Klarna offers easy monthly payment plans that work for all budgets, so you can take that well-earned holiday sooner.
  • Pay in instalments holidays: If you'd prefer to pay for your getaway in multiple transactions, holidays paid in instalments might be the best option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than all of it upfront) makes it easier to hit that "book now" button, go for a low deposit holiday payment plan from Klarna.

Where should I stay in Skokie?
A holiday in Skokie wouldn't be complete without stopping by Skokie Theatre, Sky High Sports Niles and North Shore Centre for the Performing Arts. Stay near these top sights and make sightseeing a breeze.
What are the top hotels in Skokie?
Get your holiday off to a flying start by locking in a room at Hyatt Regency Chicago. It's one of most popular properties in Skokie. Another welcoming option is The Godfrey Hotel Chicago.
How far in advance should I book my Skokie holiday?
Reserving your spot early with Expedia means one less thing to have to worry about. Many air carriers advertise tickets up to 12 months prior to departure dates. This is usually the cheapest time to book. If circumstances have left you booking late, discount tickets to Skokie sometimes emerge a few weeks before departure.
What does an Expedia Skokie travel package include?
Select from any combination of flights, hotels and rental cars. Once you've made your booking, you can also add on experiences and tours. Want to pick your airfare class? That's possible too. The choice is all yours when it comes to planning your perfect Skokie getaway.
What should I know before booking a Skokie travel package?
You'll land big savings when you bundle your flights, hotels and rental cars into a travel package. Not only that, booking everything in one place will make your trip planning easier. So why waste time or money? Whether you're putting together an upscale romantic escape or a low-cost family break, take a look at our travel packages today.
Can I choose my airline with a Skokie Expedia travel package?
Yes --- that's the beauty of an Expedia travel package. You get to decide. We have access to more than 550 partner airlines across the globe, so you have lots of choice when creating your Skokie trip.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.