BA's World Traveller Plus offers extra seat width and legroom, ideal for comfort.
BA's Club Suite provides privacy with solo pods and a door you can close.
$56+ Cheap flights from Orlando (MCO) to Chicago (CHI)
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 6/19. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
may. 25 — jun. 11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Orlando to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Orlando to Chicago are usually found in September or February, booked 46 days in advance, depart on a Friday or Thursday and return on a Tuesday
Cheap flight deals from Orlando to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Orlando (MCO) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated mayo 20, 2025.
Most accurate provider | Mytrip 3 stars |
|---|---|
Most trusted provider | Mytrip 3 stars |
Round-trip from | $104 (Cheapflightsfares) |
One-way from | $56 (Frontier) |
Popular in | March |
Cheapest in | September |
Average price | $180 |
Good round-trip deal | $152 or less |
Good one-way deal | $96 or less |
Find flight deals from Orlando to Chicago
Cheapest flights from Orlando to ChicagoExplore the most affordable flight options available from Orlando to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on mayo 20, 2025.
Explore the most affordable flight options available from Orlando to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on mayo 20, 2025.
This Cheapflightsfares deal was found by Cheapflights users on 5/20. 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.
jue. 6/195:01 amMCO - ORD
Nonstop3h 08mMultiple Airlines
mié. 6/257:56 amORD - MCO
Nonstop2h 44mMultiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$104
This Cheapflightsfares deal was found by Cheapflights users on 5/20. 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.
jue. 6/265:01 amMCO - ORD
Nonstop3h 08mFrontier
vie. 6/279:58 amORD - MCO
Nonstop2h 44mFrontier
Deal found 5/20![Frontier logo]()
$105
This Cheapflightsfares deal was found by Cheapflights users on 5/20. 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.
jue. 6/196:22 pmMCO - MDW
Nonstop2h 55mFrontier
dom. 6/229:12 pmMDW - MCO
Nonstop2h 41mFrontier
Deal found 5/20![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 5/19. 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.
sáb. 7/122:48 pmMCO - ORD
Nonstop3h 08mSpirit Airlines
mié. 7/164:36 pmORD - MCO
Nonstop2h 47mSpirit Airlines
Deal found 5/19![Spirit Airlines logo]()
$111
This Southwest deal was found by Cheapflights users on 5/18. 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.
jue. 7/179:45 amMCO - ORD
Nonstop3h 05mSouthwest
mar. 7/226:00 amORD - MCO
Nonstop2h 40mSouthwest
Deal found 5/18![Southwest logo]()
$173
This Mytrip deal was found by Cheapflights users on 5/20. 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.
jue. 6/126:30 amMCO - RFD
1 stop9h 46mMultiple Airlines
dom. 6/154:06 pmRFD - MCO
1 stop7h 14mMultiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$178
This Southwest deal was found by Cheapflights users on 5/20. 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.
mié. 7/27:45 amMCO - MDW
Nonstop2h 45mSouthwest
sáb. 7/55:10 pmMDW - MCO
1 stop4h 30mSouthwest
Deal found 5/20![Southwest logo]()
$186
This Delta deal was found by Cheapflights users on 5/19. 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.
mar. 6/246:15 amMCO - MDW
1 stop4h 26mDelta
mar. 7/1512:43 pmMDW - MCO
1 stop7h 20mDelta
Deal found 5/19![Delta logo]()
$197
This Delta deal was found by Cheapflights users on 5/20. 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.
mar. 6/105:50 pmMCO - ORD
1 stop7h 07mDelta
mié. 6/189:49 amORD - MCO
1 stop4h 43mDelta
Deal found 5/20![Delta logo]()
$213
This Mytrip deal was found by Cheapflights users on 5/20. 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.
vie. 7/48:27 amMCO - MDW
1 stop6h 37mAllegiant Air
vie. 7/1110:31 amMDW - MCO
1 stop9h 12mAllegiant Air
Deal found 5/20![Allegiant Air logo]()
$214
This American Airlines deal was found by Cheapflights users on 5/19. 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.
lun. 7/142:52 pmMCO - ORD
Nonstop3h 12mAmerican Airlines
jue. 7/176:45 amORD - MCO
Nonstop2h 39mAmerican Airlines
Deal found 5/19![American Airlines logo]()
$220
This United Airlines deal was found by Cheapflights users on 5/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/2911:00 amMCO - ORD
Nonstop3h 07mUnited Airlines
vie. 8/89:15 amORD - MCO
Nonstop2h 55mUnited Airlines
Deal found 5/19![United Airlines logo]()
$243
Cheapflights Fare Finder
Customize your flight search to find flights from Orlando to Chicago 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 mayo 20, 2025.
Use the filters below to find and compare flights from Orlando Airport to Chicago that are best for you.
Fly from
Orlando
Fly to
Chicago
Route
Depart
Return
Price
OrlandoChicago
MCO - ORD
MCOORD
Orlando
jue. 6/19
5:01 am-7:09 am
Nonstop3h 08m
Chicago O'Hare Intl
mié. 6/25
7:56 am-11:40 am
Nonstop2h 44m
$104
OrlandoChicago
MCO - ORD
MCOORD
Orlando
jue. 6/26
5:01 am-7:09 am
Nonstop3h 08m
Chicago O'Hare Intl
vie. 6/27
9:58 am-1:42 pm
Nonstop2h 44m
$105
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
jue. 6/19
6:22 pm-8:17 pm
Nonstop2h 55m
Chicago Midway
dom. 6/22
9:12 pm-12:53 am
Nonstop2h 41m
$108
OrlandoChicago
MCO - ORD
MCOORD
Orlando
sáb. 7/12
2:48 pm-4:56 pm
Nonstop3h 08m
Chicago O'Hare Intl
mié. 7/16
4:36 pm-8:23 pm
Nonstop2h 47m
$111
OrlandoChicago
MCO - ORD
MCOORD
Orlando
jue. 7/17
9:45 am-11:50 am
Nonstop3h 05m
Chicago O'Hare Intl
mar. 7/22
6:00 am-9:40 am
Nonstop2h 40m
$173
OrlandoChicago
MCO - RFD
MCORFD
Orlando
jue. 6/12
6:30 am-3:16 pm
1 stop9h 46m
Chicago Greater Rockford
dom. 6/15
4:06 pm-12:20 am
1 stop7h 14m
$178
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
mié. 7/2
7:45 am-9:30 am
Nonstop2h 45m
Chicago Midway
sáb. 7/5
5:10 pm-10:40 pm
1 stop4h 30m
$186
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
mar. 6/24
6:15 am-11:59 am
1 stop6h 44m
Chicago Midway
mié. 7/2
4:26 pm-12:14 am
1 stop6h 48m
$197
OrlandoChicago
MCO - ORD
MCOORD
Orlando
mar. 6/10
5:50 pm-11:57 pm
1 stop7h 07m
Chicago O'Hare Intl
mié. 6/18
9:49 am-3:32 pm
1 stop4h 43m
$213
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
vie. 7/4
8:27 am-2:04 pm
1 stop6h 37m
Chicago Midway
vie. 7/11
10:31 am-8:43 pm
1 stop9h 12m
$214
Showing 1-10 of 27 results
Compare providers for flights from Orlando to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Orlando to Chicago in May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Orlando Airport-Chicago flights, users find the pricing of Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on Orlando Airport-Chicago flight deals on Cheapflights vs. Mytrip >95% of the time. Price accuracy is based on data collected from Orlando Airport-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Orlando Airport-Chicago flights, Cheapflights users trust Mytrip the most. Mytrip has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Orlando Airport-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
The best insider tips for Orlando Airport to Chicago flights
Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Orlando Airport to Chicago trip
Airlines
![British Airways]()
British Airways
![Frontier]()
Frontier
Frontier's UpFront Plus seats guarantee an empty middle seat for more space.
Frontier's Economy Bundle includes a carry-on bag, seat selection, and no change fees.
![Spirit Airlines]()
Spirit Airlines
Spirit's Big Front Seats offer 11 inches more legroom and larger tray tables.
Spirit's self-service bag drop saves time; print your boarding pass beforehand to avoid charges.
![United Airlines]()
United Airlines
Basic Economy allows only a personal item; no carry-on bags unless exceptions apply.
Economy Plus offers extra legroom seats at the front of the economy cabin.
Airports
Our travel experts
Best time to book a flight from Orlando to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Orlando 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 Orlando Airport to Chicago
How far ahead should I book a flight from Orlando Airport to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Orlando to Chicago. Price data was last updated on May 16, 2025.
The best time to book flights from Orlando Airport to Chicago is 46 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Orlando Airport to Chicago?
Currently, August is the cheapest month in which you can book a flight from Orlando Airport to Chicago (average of $245). Flying from Orlando Airport to Chicago in March is currently the most expensive (average of $321). 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 MCO to CHI?
Find hourly flight availability from Orlando to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated mayo 20, 2025.
It’s typically best to fly out from Orlando Airport to Chicago in the evening. Doing so could potentially save you 73% on the flight price compared to flying at noon, which is usually more expensive.
What is the cheapest day to fly from Orlando Airport to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Orlando to Chicago. Price data was last updated on May 18, 2025.
Travelers seeking maximum savings on their Orlando Airport to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Wednesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Orlando Airport to Chicago
Explore weekly flight availability from Orlando to Chicago. 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 mayo 20, 2025.
The most flights from MCO to CHI are scheduled on a Monday (65 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (18 on average).
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated mayo 20, 2025.
Get a feel of what it's like to fly with Southwest, Delta and United Airlines from Orlando to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Food
7.1
Entertainment
7.6
Overall
8.0
Boarding
8.2
Crew
8.6
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Comfort
8.0
Food
7.1
Entertainment
7.6
Overall
8.0
Boarding
8.2
Crew
8.6
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Comfort
8.0
Food
7.1
Entertainment
7.6
Overall
8.0
Boarding
8.2
Crew
8.6
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Comfort
8.0
Food
7.1
Entertainment
7.6
Overall
8.0
Boarding
8.2
Crew
8.6
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Comfort
8.0
Food
7.1
Entertainment
7.6
Overall
8.0
Boarding
8.2
Crew
8.6
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Comfort
8.0
Food
7.1
Entertainment
7.6
Overall
8.0
Boarding
8.2
Crew
8.6
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Related info for your journey
Find useful and relevant information for your journey from Orlando to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Orlando Airport?
Book flights to Orlando Airport if you plan to visit one of these locationsMerrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Orlando to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from Orlando to Chicago
Discover the top 6 airlines that operate flights from Orlando to Chicago. 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 mayo 20, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$66 | Average$166 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$72 | Average$164 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$114 | Average$407 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$157 | Average$331 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$159 | Average$287 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$184 | Average$351 | FlexibilityNo cancel fee | On-time63% |