Skokie Holidays

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    Save up to S$1,300 when you book a flight and hotel together*

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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 S$177 per night from 22 Nov to 23 Nov
S$177
22 Nov - 23 Nov
includes taxes & fees
8/10 Very good! (10,180 reviews)
"This is an older hotel with a lot of rooms, so I am never sure what to expect -- but this was a good stay. We stored our bags at the beginning and end of our stay with no problems. Our room was in the north tower and it had been refurbished. Beds were comfortable enough, and it was clean even if ..."

Reviewed on 12 Nov, 2026

Congress Plaza Hotel
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 S$177 per night from 15 Nov to 16 Nov
S$177
15 Nov - 16 Nov
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$162 per night from 10 Dec to 11 Dec
S$162
10 Dec - 11 Dec
includes taxes & fees
8.8/10 Excellent! (5,597 reviews)
"."

Reviewed on 12 Nov, 2026

River Hotel
See all 4,725 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

North Shore Center for the Performing Arts

8.0/10 (61 reviews)
This intimate cultural venue houses two theatres showcasing diverse performances. Enjoy excellent acoustics and sightlines before exploring nearby dining options for a complete evening experience.
See properties

What to do in Skokie

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

S$31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

S$51
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

S$54
per adult
86% of travellers recommend
Skydeck Chicago at Willis Tower
See all activities in Skokie

Frequently asked questions

How much does a Skokie holiday package cost?
Offering excellent value package deals 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.