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Ocala

$49+ Cheap flights from Chicago (CHI) to Ocala, FL

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Ocala are usually found in September or July, booked 85 days in advance, depart on a Tuesday or Thursday and return on a Friday

Cheap flight deals from Chicago to Ocala

Keep the following information in mind while searching for Chicago to Ocala flight deals. Data was last updated September 16, 2025.

Round-trip from

$92
(Cheapflightsfares)

One-way from

$49
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$203
From Chicago (CHI) to Ocala
Search Deals
One-way flight from Chicago (CHI) to Ocala
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Chicago to Ocala

Cheapest flights from Chicago to Ocala
Explore the most affordable flight options available from Chicago to Ocala. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/48:00 amORD - MCO
Nonstop2h 57mFrontier
Sat 10/111:28 pmMCO - ORD
Nonstop3h 11mFrontier
Deal found 9/15$92
This Cheapflightsfares deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/86:00 amORD - MCO
Nonstop2h 44mSpirit Airlines
Fri 10/107:30 pmMCO - ORD
Nonstop3h 03mSpirit Airlines
Deal found 9/15$93
This Spirit deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/86:58 pmORD - MCO
Nonstop2h 52mSpirit Airlines
Tue 10/143:53 pmMCO - ORD
Nonstop3h 00mSpirit Airlines
Deal found 9/13$94
This Priceline deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/268:49 pmORD - MCO
Nonstop2h 46mMultiple Airlines
Sat 9/272:07 pmMCO - ORD
Nonstop3h 05mMultiple Airlines
Deal found 9/15$95
This Priceline deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/177:51 pmORD - MCO
Nonstop2h 52mMultiple Airlines
Thu 10/236:05 amMCO - ORD
Nonstop3h 09mMultiple Airlines
Deal found 9/15$96
This Cheapflightsfares deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/45:17 pmORD - MCO
Nonstop2h 49mSpirit Airlines
Tue 10/73:53 pmMCO - ORD
Nonstop3h 00mSpirit Airlines
Deal found 9/16$97
This Trip.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/177:51 pmORD - MCO
Nonstop2h 52mMultiple Airlines
Sat 10/184:23 pmMCO - ORD
Nonstop3h 10mMultiple Airlines
Deal found 9/13$98
This Cheapflightsfares deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/411:21 amMDW - MCO
Nonstop2h 43mFrontier
Mon 10/65:35 amMCO - MDW
Nonstop2h 48mFrontier
Deal found 9/14$99
This Cheapflightsfares deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/510:18 amORD - MCO
Nonstop2h 46mSpirit Airlines
Mon 12/87:15 pmMCO - ORD
Nonstop3h 08mSpirit Airlines
Deal found 9/14$99
This Priceline deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/298:19 amMDW - MCO
Nonstop2h 41mFrontier
Sun 10/57:25 amMCO - MDW
Nonstop2h 53mFrontier
Deal found 9/13$100
This Cheapflightsfares deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/228:49 pmORD - MCO
Nonstop2h 46mFrontier
Sat 9/271:02 pmMCO - ORD
Nonstop3h 15mFrontier
Deal found 9/15$100
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/216:00 amORD - MCO
Nonstop2h 44mMultiple Airlines
Wed 10/2212:58 pmMCO - ORD
Nonstop3h 10mMultiple Airlines
Deal found 9/14$101

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Ocala that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 16, 2025.
Use the filters below to find and compare flights from Chicago to Ocala that are best for you.

Fly from

Chicago

Fly to

Ocala

Route

Depart

Return

Price

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Thu 10/23

6:58 pm-10:50 pm

Nonstop2h 52m

Orlando

Tue 10/28

2:26 pm-4:23 pm

Nonstop2h 57m

$120

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 10/14

11:40 am-3:10 pm

Nonstop2h 30m

Orlando

Thu 10/16

7:30 pm-9:15 pm

Nonstop2h 45m

$158

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 10/19

8:55 pm-12:30 am

Nonstop2h 35m

Orlando

Wed 10/22

12:15 pm-2:00 pm

Nonstop2h 45m

$158

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 11/11

1:56 pm-10:09 am

1 stop19h 13m

Orlando

Fri 11/14

5:25 am-10:08 pm

1 stop17h 43m

$163

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 10/13

8:45 pm-12:15 am

Nonstop2h 30m

Orlando

Thu 10/16

6:35 am-8:20 am

Nonstop2h 45m

$169

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 12/6

12:30 pm-6:35 pm

1 stop5h 05m

Orlando

Fri 12/12

6:55 am-8:45 am

Nonstop2h 50m

$184

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 10/28

8:05 pm-11:35 pm

Nonstop2h 30m

Orlando

Fri 10/31

7:20 am-10:40 am

1 stop4h 20m

$187

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 12/2

6:15 pm-10:00 pm

Nonstop2h 45m

Orlando

Fri 12/5

4:55 pm-9:05 pm

1 stop5h 10m

$188

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 10/6

7:05 am-10:35 am

Nonstop2h 30m

Orlando

Mon 10/13

6:35 am-8:20 am

Nonstop2h 45m

$188

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 11/15

2:30 pm-8:39 pm

1 stop5h 09m

Orlando

Tue 11/18

6:15 am-10:19 am

1 stop5h 04m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 39 results
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Best time to book a flight from Chicago to Ocala

Have a flexible travel schedule? Discover the best time to fly to Ocala from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Ocala

How far ahead should I book a flight from Chicago to Ocala?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Ocala. Price data was last updated on September 12, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Ocala, you should look to book at least 85 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago to Ocala?

Currently, May is the cheapest month in which you can book a flight from Chicago to Ocala (average of $206). Flying from Chicago to Ocala in November is currently the most expensive (average of $289). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to OC4?

Find hourly flight availability from Chicago to Ocala. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

When flying from Chicago to Ocala, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Chicago to Ocala?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Ocala. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Ocala flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Ocala

Explore weekly flight availability from Chicago to Ocala. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 16, 2025.

The most flights from CHI to OC4 are scheduled on a Monday (64 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (44 on average).

Reviews of airlines servicing Ocala

Get insights into the airlines that provide service to Ocala. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Ocala. Reviews last updated September 16, 2025.
See what other customers who have flown with Southwest, United Airlines, and American Airlines from Chicago to Ocala have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
United Airlines
7.4
Good
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Spirit Airlines
6.3
Okay
8,019 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Frontier
5.8
Fair
3,174 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Ocala. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Ocala?

    There are many flights that can get you from Chicago to Ocala in 2h 30m. Fly via Spirit Airlines, Southwest, or Frontier to get the fastest option. The distance between Chicago and Ocala is about 990 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most reliable airlines from Chicago to Ocala?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Ocala on time: Copa Airlines (84%), Spirit Airlines (82%), Air Canada (78%).

  • What are the cheapest flights from Chicago to Ocala?

    While on average a flight from Chicago to Ocala is generally $434, our data shows the cheapest flight currently is $45. When looking at the most popular route, (Chicago O'Hare Intl - Orlando), you can expect to pay $84 for that flight.

  • Can I find deals for flights from Chicago to Ocala that include hotel bookings?

    Yes. In addition to deals on Chicago to Ocala flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Ocala?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Ocala.

  • Can I find deals for business class flights from Chicago to Ocala?

    Yes. Cheapflights offers flight deals from Chicago to Ocala by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Ocala?

    Currently, May is the cheapest month in which you can book a flight from Chicago to Ocala (average of $206). Flying from Chicago to Ocala in November is currently the most expensive (average of $289). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top 7 airlines flying from Chicago to Ocala

Discover the top 7 airlines that operate flights from Chicago to Ocala. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$215FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$63Average$177FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$112Average$189FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$157Average$352FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$160Average$407FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$163Average$348FlexibilityNo cancel feeOn-time69%
DeltaCheapest$176Average$440FlexibilityNo cancel feeOn-timeN/A

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