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$51+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Ocala are usually found in May or July, booked 85 days in advance, depart on a Tuesday or Saturday 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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$113
(Kiwi.com)

One-way from

$52
(Trip.com)

Popular in

March

Cheapest in

May

Average price

$208
Provider with most accurate pricing for Chicago (CHI)-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Orlando (ORL) flights.
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From Chicago (CHI) to Ocala
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One-way flight from Chicago (CHI) to Ocala
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Highest demand for flights based on searches. 5% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Mon 5/267:47 amORD - MCO
Nonstop2h 39mMultiple Airlines
Sat 5/319:57 pmMCO - ORD
Nonstop3h 07mMultiple Airlines
Deal found 4/30$113
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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.
Thu 5/229:12 pmMDW - MCO
Nonstop2h 45mFrontier
Sun 5/256:20 pmMCO - MDW
Nonstop2h 57mFrontier
Deal found 4/30$114
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Mon 5/267:47 amORD - MCO
Nonstop2h 39mSpirit Airlines
Sat 5/319:25 pmMCO - ORD
Nonstop3h 04mSpirit Airlines
Deal found 4/30$117
This Frontier deal was found by Cheapflights users on 4/30. 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.
Fri 5/305:14 pmORD - MCO
Nonstop2h 57mFrontier
Sun 6/110:17 pmMCO - ORD
Nonstop3h 19mFrontier
Deal found 4/30$118
This Southwest deal was found by Cheapflights users on 4/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/77:05 pmMDW - MCO
Nonstop2h 40mSouthwest
Tue 6/106:20 amMCO - MDW
Nonstop2h 50mSouthwest
Deal found 4/29$197
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/245:55 pmMDW - MCO
1 stop4h 59mDelta
Sun 5/256:15 amMCO - MDW
1 stop6h 38mDelta
Deal found 4/29$200
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2410:35 amORD - MCO
1 stop7h 19mDelta
Sat 7/268:50 amMCO - ORD
1 stop5h 00mDelta
Deal found 4/30$208
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/3011:45 amORD - MCO
Nonstop2h 39mAmerican Airlines
Wed 9/35:58 pmMCO - ORD
1 stop4h 27mAmerican Airlines
Deal found 4/30$223
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/68:36 pmMDW - MCO
1 stop11h 25mAllegiant Air
Mon 6/98:24 amMCO - MDW
1 stop6h 39mAllegiant Air
Deal found 4/30$225

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 May 1, 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

Mon 5/26

7:47 am-11:26 am

Nonstop2h 39m

Orlando

Sat 7/26

6:05 am-8:07 am

Nonstop3h 02m

$113

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Thu 5/22

9:12 pm-12:57 am

Nonstop2h 45m

Orlando

Sun 5/25

6:20 pm-8:17 pm

Nonstop2h 57m

$114

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Mon 6/2

5:14 pm-9:15 pm

Nonstop3h 01m

Orlando

Thu 6/5

9:57 pm-12:10 am

Nonstop3h 13m

$116

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Mon 5/26

7:47 am-11:26 am

Nonstop2h 39m

Orlando

Sat 5/31

9:25 pm-11:29 pm

Nonstop3h 04m

$117

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 6/7

7:05 pm-10:45 pm

Nonstop2h 40m

Orlando

Tue 6/10

6:20 am-8:10 am

Nonstop2h 50m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 5/24

5:55 pm-11:54 pm

1 stop4h 59m

Orlando

Sun 5/25

6:15 am-11:53 am

1 stop6h 38m

$200

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 5/24

10:35 am-6:54 pm

1 stop7h 19m

Orlando

Sat 7/26

8:50 am-12:50 pm

1 stop5h 00m

$208

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 6/6

8:36 pm-9:01 am

1 stop11h 25m

Orlando

Mon 6/9

8:24 am-2:03 pm

1 stop6h 39m

$225

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Wed 6/4

1:50 pm-10:15 pm

2 stops7h 25m

Orlando

Tue 6/10

9:15 am-12:45 pm

1 stop4h 30m

$240

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 6/21

6:25 pm-11:59 pm

1 stop4h 34m

Orlando

Sat 6/28

5:00 am-9:37 am

1 stop5h 37m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 25 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 April 25, 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 May 1, 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 Tuesday afternoons when fares are most often at their lowest. Monday mornings 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 May 1, 2025.

The most flights from CHI to OC4 are scheduled on a Wednesday (56 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (17 on average).

Rainfall in Ocala by month

Plan your trip to Ocala by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Ocala ranges from 2.4 - 8.7 inches per month. June is typically the wettest month, when rainfall can reach 8.7 in. November is typically the driest time to visit Ocala when rainfall is around 2.4 in.

Temperature in Ocala by month

Plan your trip to Ocala by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Ocala, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 60.8 F).

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 May 1, 2025.
To help decide which airline to fly from Chicago to Ocala, see what other customers have to say about Alaska Airlines, Southwest and Delta. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,968 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,968 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,294 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Avelo Airlines
7.5
Good
Alaska Airlines
8.0
Very good
9,968 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

  • 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 $52 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $55 and Southwest from $90 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: Southwest (88%), Azul (85%), Copa Airlines (83%).

  • What are the cheapest flights from Chicago to Ocala?

    While on average a flight from Chicago to Ocala is generally $537, our data shows the cheapest flight currently is $50. When looking at the most popular route, (Chicago O'Hare Intl - Orlando), you can expect to pay $86 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.

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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$42Average$195FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$64Average$174FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$112Average$209FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$128Average$341FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$159Average$419FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$180Average$397FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$443FlexibilityNo cancel feeOn-timeN/A

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