Kankakee Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Kankakee

Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

3.5 out of 5
11111 Wilson Road, New Buffalo, MI
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,430 reviews)
"Nice resort!"

Reviewed on 30 Jul, 2025

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Four Winds Casino Resort – New Buffalo
Doubletree Hotel South Bend

Doubletree Hotel South Bend

4 out of 5
123 N Dr. Martin Luther King BLVD, South Bend, IN
Fully refundableReserve now, pay when you stay
The price is S$158 per night from 1 Sept to 2 Sept
S$158
1 Sept - 2 Sept
includes taxes & fees
7.6/10 Good! (1,001 reviews)
"The people at the front desk were wonderful! They represent your hotel with friendliness and great service!"

Reviewed on 1 Aug, 2025

Doubletree Hotel South Bend
Four Winds Casino South Bend

Four Winds Casino South Bend

3 out of 5
3000 Prairie Ave, South Bend, IN
Fully refundableReserve now, pay when you stay
The price is S$173 per night from 4 Aug to 5 Aug
S$173
4 Aug - 5 Aug
includes taxes & fees
9.6/10 Exceptional! (578 reviews)
"There should be a restaurant opened every day 24 hrs. There needs to be a ride available inside for people who have trouble walking etc. Everyone there was super nice and helpful. I will stay here again."

Reviewed on 31 Jul, 2025

Four Winds Casino South Bend
See all 551 properties in Kankakee
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.

Frequently asked questions

How much does a Kankakee holiday package cost?
You'll find cheap prices on Expedia for your Kankakee escape. However, factors like your choice of hotel, the season and length of stay will influence how much your holiday to Kankakee costs.
What are the cheapest months to go to Kankakee?
If you're looking to score a cheap Kankakee holiday package, consider visiting in January, February and November. You'll usually find lower rates on flights and hotels during these quieter months — ideal for travellers wishing to save money.
How many days is enough for Kankakee?
With a well-organised itinerary, you can easily tick off the most popular Kankakee sights in a few days. But if you prefer to discover hidden gems or go on day trips, consider booking your Kankakee holiday for longer.
How to find the best Kankakee package deals?
Use Expedia's filters to find some unbeatable Kankakee package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Kankakee package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your holiday package as early as possible.
Is it cheaper to book a Kankakee holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking flights and hotels separately. Better still, you can customise your Kankakee trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Kankakee?
If you're planning an impromptu Kankakee adventure, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Kankakee?

  1. Choose when to go: Check your diary and pack your bags. Your favourite season and the type of activities available will also help you decide when to escape to Kankakee.
  2. Figure out your budget: Make sure you have enough money to pay for everything from dining out and transportation to experiences and flights. Your accommodation will likely be the biggest expense during your trip to Kankakee.
  3. Decide how long to go for: Now that you're more familiar with Kankakee, you can figure out the right length of your holiday. Create a draft plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a tailored Kankakee holiday package.

* 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.