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Ocala

$50+ 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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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

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 December 18, 2025.

This Frontier deal was found by Cheapflights users on 12/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:10 pmMDW - MCO
Nonstop2h 48mFrontier
Thu 1/158:30 amMCO - MDW
Nonstop3h 02mFrontier
Deal found 12/15$109
This Frontier deal was found by Cheapflights users on 12/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:23 amORD - MCO
Nonstop2h 55mFrontier
Thu 1/155:16 pmMCO - ORD
Nonstop3h 25mFrontier
Deal found 12/15$109
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:23 amORD - MCO
Nonstop2h 55mMultiple Airlines
Wed 1/1411:04 amMCO - ORD
Nonstop3h 09mMultiple Airlines
Deal found 12/15$115
This Frontier deal was found by Cheapflights users on 12/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:10 pmMDW - MCO
Nonstop2h 48mFrontier
Fri 1/99:13 pmMCO - MDW
Nonstop2h 56mFrontier
Deal found 12/16$119
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:20 amORD - MCO
Nonstop2h 52mMultiple Airlines
Sat 1/104:48 pmMCO - ORD
Nonstop3h 29mMultiple Airlines
Deal found 12/16$121
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:23 amORD - MCO
Nonstop2h 55mMultiple Airlines
Fri 1/163:43 pmMCO - ORD
Nonstop3h 09mMultiple Airlines
Deal found 12/15$126
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:20 amORD - MCO
Nonstop2h 52mSpirit Airlines
Wed 1/74:56 pmMCO - ORD
Nonstop3h 06mSpirit Airlines
Deal found 12/16$127
This Frontier deal was found by Cheapflights users on 12/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:10 pmMDW - MCO
Nonstop2h 48mFrontier
Wed 1/146:10 amMCO - MDW
1 stop5h 21mFrontier
Deal found 12/15$129
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Wed 12/316:05 amORD - MCO
1 stop14h 20mMultiple Airlines
Wed 1/74:56 pmMCO - ORD
Nonstop3h 06mMultiple Airlines
Deal found 12/17$131
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:12 amMDW - MCO
1 stop14h 13mMultiple Airlines
Fri 1/99:13 pmMCO - MDW
Nonstop2h 56mMultiple Airlines
Deal found 12/16$134
This Frontier deal was found by Cheapflights users on 12/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:15 amMDW - MCO
1 stop7h 21mFrontier
Wed 12/317:58 pmMCO - MDW
Nonstop3h 00mFrontier
Deal found 12/15$136
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:50 amORD - MCO
1 stop15h 30mMultiple Airlines
Tue 1/2011:04 amMCO - ORD
Nonstop3h 09mMultiple Airlines
Deal found 12/16$137

Find flight deals from Chicago to Ocala

Keep the following information in mind while searching for Chicago to Ocala flight deals. Data was last updated December 18, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$91
(Kiwi.com)

One-way from

$50
(CheapOair)

Popular in

March

Cheapest in

September

Average price

$311
Provider with most accurate pricing for Chicago (CHI)-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Orlando (ORL) flights.
Search Deals
From Chicago (CHI) to Ocala
Search Deals
One-way flight from Chicago (CHI) to Ocala
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 18, 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

MDW - MCO

MDWMCO

Chicago Midway

Fri 1/23

5:01 pm-12:31 am

1 stop6h 30m

Orlando

Fri 1/30

5:49 pm-7:52 pm

Nonstop3h 03m

$150

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Fri 1/30

5:59 pm-9:50 pm

Nonstop2h 51m

Orlando

Tue 2/3

12:30 pm-2:39 pm

Nonstop3h 09m

$177

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 1/25

3:10 pm-9:30 pm

1 stop5h 20m

Orlando

Wed 1/28

4:45 pm-6:40 pm

Nonstop2h 55m

$187

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 1/17

9:45 am-5:00 pm

1 stop6h 15m

Orlando

Wed 1/21

7:25 am-9:20 am

Nonstop2h 55m

$187

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Fri 1/23

8:02 pm-12:01 am

Nonstop2h 59m

Orlando

Fri 1/30

12:30 pm-2:39 pm

Nonstop3h 09m

$188

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 1/25

6:00 pm-9:40 pm

Nonstop2h 40m

Orlando

Sat 1/31

2:40 pm-4:35 pm

Nonstop2h 55m

$188

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Thu 1/1

5:30 am-12:04 pm

1 stop5h 34m

Orlando

Sun 1/18

5:30 am-10:07 am

1 stop5h 37m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 1/31

4:30 pm-9:49 pm

1 stop4h 19m

Orlando

Sat 2/7

6:15 am-9:53 am

1 stop4h 38m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 1/18

9:32 am-5:10 pm

1 stop6h 38m

Orlando

Tue 1/20

6:35 pm-10:22 pm

1 stop4h 47m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 1/6

3:15 pm-6:50 pm

Nonstop2h 35m

Orlando

Tue 1/13

7:05 pm-9:00 pm

Nonstop2h 55m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 43 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 December 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, March is the cheapest month in which you can book a flight from Chicago to Ocala (average of $53). Flying from Chicago to Ocala in June is currently the most expensive (average of $108). 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 December 18, 2025.

It’s typically best to fly out from Chicago to Ocala in the evening. Doing so could potentially save you 25% on the flight price compared to flying at noon, which is usually more expensive.

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 Friday evenings when fares are most often at their lowest. Monday 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 December 18, 2025.

The most flights from CHI to OC4 are scheduled on a Wednesday (60 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 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 December 18, 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
7.9
Good
4,250 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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
9,091 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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
11,054 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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
8,190 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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
3,081 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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 51m. Fly via Frontier, United Airlines, or Southwest to get the fastest option. The distance between Chicago and Ocala is about 1006 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chicago to Ocala one-way?

    One-way options have recently been found by users for as low as $37 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $42 and Southwest from $78 one-way.

  • 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 (88%), Volaris (83%), Azul (81%).

  • What are the cheapest flights from Chicago to Ocala?

    While on average a flight from Chicago to Ocala is generally $464, our data shows the cheapest flight currently is $48. When looking at the most popular route, (Chicago O'Hare Intl - Orlando), you can expect to pay $61 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, March is the cheapest month in which you can book a flight from Chicago to Ocala (average of $53). Flying from Chicago to Ocala in June is currently the most expensive (average of $108). 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 8 airlines flying from Chicago to Ocala

Discover the top 8 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$54Average$210FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$63Average$180FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$97Average$197FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$146Average$339FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$156Average$361FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$157Average$333FlexibilityNo cancel feeOn-time69%
DeltaCheapest$176Average$422FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$195Average$296FlexibilityNo cancel feeOn-time62%

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