Cheap Flights from Orlando, FL to Chicago, IL from $53

One way Round trip

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Return flight: Chicago – Orlando

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On Cheapflightsplus.com you will find 33 direct and 729 connecting flights from Orlando to Chicago. You can compare airfare deals from 14 airlines and multiple travel sites from $53, book and save on cheap plane tickets and last minute offers. Also check out MCO-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Orlando to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $53 (one-way), $91 (round-trip).

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Best Flights from Orlando to Chicago Today

Take a look at the list of non stop flights and flights with layovers from Orlando to Chicago with the lowest price of $53. The fastest direct flight takes 2h 48m and the fastest connecting – 4h 17m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $53 Find flight	22:59 Orlando Orlando Int.	00:59+1 день Chicago O'Hare International	3h 0m	Frontier Airlines	F93043
from $91 Find flight	10:35 Orlando Orlando Int.	12:23 Chicago Midway	2h 48m	Frontier Airlines	F91457
from $95 Find flight	18:11 Orlando Orlando Int.	20:15 Chicago O'Hare International	3h 4m	Spirit Airlines	NK1147
from $136 Find flight	18:54 Orlando Orlando Int.	20:58 Chicago O'Hare International	3h 4m	Spirit Airlines	NK1842
from $147 Find flight	12:30 Orlando Orlando Int.	14:32 Chicago O'Hare International	3h 2m	United Airlines	UA2475
from $169 Find flight	07:00 Orlando Orlando Int.	09:13 Chicago O'Hare International	3h 13m	American Airlines	AA598
from $171 Find flight	09:30 Orlando Orlando Int.	11:33 Chicago O'Hare International	3h 3m	United Airlines	UA2341
from $174 Find flight	07:10 Orlando Orlando Int.	09:05 Chicago Midway	2h 55m	Southwest Airlines	WN898
from $202 Find flight	17:16 Orlando Orlando Int.	19:31 Chicago O'Hare International	3h 15m	Frontier Airlines	F92041
from $211 Find flight	17:00 Orlando Orlando Int.	18:50 Chicago Midway	2h 50m	Southwest Airlines	WN2401
from $53 Find flight	05:00 Orlando Orlando Int.	10:05 Chicago O'Hare International	6h 5m layover 1h 5m - New York	Spirit Airlines	NK316 NK779
from $61 Find flight	15:36 Orlando Orlando Int.	22:52 Chicago O'Hare International	8h 16m layover 2h 49m - Newark	Spirit Airlines	NK994 NK329
from $67 Find flight	20:59 Orlando Orlando Int.	15:50+1 день Chicago Midway	19h 51m layover 13h 12m - Denver	Frontier Airlines	F93311 F91228
from $70 Find flight	17:00 Orlando Orlando Int.	20:49 Chicago Midway	4h 49m layover 1h 8m - Atlanta	Frontier Airlines	F94025 F92779
from $78 Find flight	13:15 Orlando Orlando Int.	12:04+1 день Chicago O'Hare International	23h 49m layover 6h 14m - Houston 7h 57m - Las Vegas	Spirit Airlines	NK197 NK490 NK187
from $108 Find flight	06:57 Orlando Orlando Int.	18:41 Chicago O'Hare International	12h 44m layover 2h 12m - Boston 0h 41m - Miami	Spirit Airlines	NK2068 NK2887 NK157

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on May 06, 2025

Flight Schedule Orlando (Florida) to Chicago (Illinois)

Full flight schedule will help you in detecting at what time planes fly from Orlando to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.

Departure	Flight Details	Flight Duration	Price
05:10 — 07:18	05:10 — 07:18 NK1683 Spirit Airlines Orlando — Chicago	3h 8m	Find flight from$142
07:00 — 09:13	07:00 — 09:13 AA598 American Airlines Orlando — Chicago	3h 13m	Find flight from$169
07:10 — 09:05	07:10 — 09:05 WN898 Southwest Airlines Orlando — Chicago	2h 55m	Find flight from$174
07:30 — 09:33	07:30 — 09:33 UA2673 United Airlines Orlando — Chicago	3h 3m	Find flight from$147
09:00 — 12:50	09:00 — 12:50 WN3094 Southwest Airlines Orlando — Chicago	4h 50m	Find flight from$413
09:30 — 11:33	09:30 — 11:33 UA395 United Airlines Orlando — Chicago	3h 3m	Find flight from$147
09:30 — 11:33	09:30 — 11:33 UA2341 United Airlines Orlando — Chicago	3h 3m	Find flight from$171
10:25 — 12:15	10:25 — 12:15 WN546 Southwest Airlines Orlando — Chicago	2h 50m	Find flight from$288
10:30 — 12:33	10:30 — 12:33 UA1485 United Airlines Orlando — Chicago	3h 3m	Find flight from$147
10:35 — 12:23	10:35 — 12:23 F91457 Frontier Airlines Orlando — Chicago	2h 48m	Find flight from$91
11:00 — 13:06	11:00 — 13:06 UA374 United Airlines Orlando — Chicago	3h 6m	Find flight from$173
11:00 — 13:03	11:00 — 13:03 UA503 United Airlines Orlando — Chicago	3h 3m	Find flight from$216
12:30 — 14:32	12:30 — 14:32 UA2475 United Airlines Orlando — Chicago	3h 2m	Find flight from$147
12:40 — 14:30	12:40 — 14:30 WN4265 Southwest Airlines Orlando — Chicago	2h 50m	Find flight from$252
12:58 — 14:59	12:58 — 14:59 AA985 American Airlines Orlando — Chicago	3h 1m	Find flight from$273
13:57 — 16:08	13:57 — 16:08 NK223 Spirit Airlines Orlando — Chicago	3h 11m	Find flight from$142
14:25 — 16:38	14:25 — 16:38 UA1492 United Airlines Orlando — Chicago	3h 13m	Find flight from$384
14:35 — 16:38	14:35 — 16:38 UA2061 United Airlines Orlando — Chicago	3h 3m	Find flight from$173
14:45 — 16:52	14:45 — 16:52 NK506 Spirit Airlines Orlando — Chicago	3h 7m	Find flight from$142
15:30 — 19:50	15:30 — 19:50 WN1462 Southwest Airlines Orlando — Chicago	5h 20m	Find flight from$348
15:40 — 17:30	15:40 — 17:30 WN1523 Southwest Airlines Orlando — Chicago	2h 50m	Find flight from$252
15:50 — 18:55	15:50 — 18:55 WN3655 Southwest Airlines Orlando — Chicago	4h 5m	Find flight from$413
16:33 — 18:35	16:33 — 18:35 UA1828 United Airlines Orlando — Chicago	3h 2m	Find flight from$147
16:55 — 19:00	16:55 — 19:00 AA1247 American Airlines Orlando — Chicago	3h 5m	Find flight from$273
17:00 — 18:50	17:00 — 18:50 WN2401 Southwest Airlines Orlando — Chicago	2h 50m	Find flight from$211
17:16 — 19:31	17:16 — 19:31 F92041 Frontier Airlines Orlando — Chicago	3h 15m	Find flight from$202
18:00 — 20:03	18:00 — 20:03 UA2000 United Airlines Orlando — Chicago	3h 3m	Find flight from$171
18:11 — 20:15	18:11 — 20:15 NK1147 Spirit Airlines Orlando — Chicago	3h 4m	Find flight from$95
18:54 — 20:58	18:54 — 20:58 NK1842 Spirit Airlines Orlando — Chicago	3h 4m	Find flight from$136
19:34 — 21:44	19:34 — 21:44 UA2677 United Airlines Orlando — Chicago	3h 10m	Find flight from$175
20:35 — 22:25	20:35 — 22:25 WN2836 Southwest Airlines Orlando — Chicago	2h 50m	Find flight from$194
21:03 — 23:16	21:03 — 23:16 F93045 Frontier Airlines Orlando — Chicago	3h 13m	Find flight from$103
22:59 — 00:59 +1 day	22:59 — 00:59 F93043 Frontier Airlines Orlando — Chicago	3h	Find flight from$53
05:00 — 10:05	05:00 — 07:30 NK316 Spirit Airlines Orlando — New York 1h 5m stop 08:35 — 10:05 NK779 Spirit Airlines New York — Chicago	6h 5m including layover	Find flight from$53
05:00 — 13:44	05:00 — 07:30 NK316 Spirit Airlines Orlando — Newark 4h 38m stop 12:08 — 13:44 NK329 Spirit Airlines Newark — Chicago	9h 44m including layover	Find flight from$86
06:00 — 13:06	05:10 — 07:22 F91481 Frontier Airlines Orlando — Dallas 2h 27m stop 14:04 — 16:22 F91888 Frontier Airlines Dallas — Chicago	8h 6m including layover	Find flight from$91
06:20 — 14:00	08:05 — 10:20 F91733 Frontier Airlines Orlando — Denver 1h 47m stop 13:29 — 17:05 F93174 Frontier Airlines Denver — Chicago	8h 40m including layover	Find flight from$87
08:59 — 16:56	08:59 — 10:44 F91563 Frontier Airlines Orlando — Atlanta 4h 56m stop 15:40 — 16:56 F92007 Frontier Airlines Atlanta — Chicago	8h 57m including layover	Find flight from$100
09:37 — 17:30	09:37 — 11:52 F91733 Frontier Airlines Orlando — Denver 2h 2m stop 13:54 — 17:30 F92048 Frontier Airlines Denver — Chicago	8h 53m including layover	Find flight from$87
09:37 — 09:47 +1 day	09:37 — 11:52 F91733 Frontier Airlines Orlando — Denver 18h 18m stop 06:10 — 09:47 F91484 Frontier Airlines Denver — Chicago	25h 10m including layover	Find flight from$93
10:26 — 16:56	10:26 — 12:13 F93507 Frontier Airlines Orlando — Atlanta 3h 27m stop 15:40 — 16:56 F93395 Frontier Airlines Atlanta — Chicago	7h 30m including layover	Find flight from$88
11:30 — 18:12	11:30 — 14:03 F92506 Frontier Airlines Orlando — Philadelphia 2h 47m stop 16:50 — 18:12 F94367 Frontier Airlines Philadelphia — Chicago	7h 42m including layover	Find flight from$87
12:00 — 22:06	12:00 — 14:35 NK921 Spirit Airlines Orlando — New York 5h 54m stop 20:29 — 22:06 NK3386 Spirit Airlines New York — Chicago	11h 6m including layover	Find flight from$89
12:27 — 17:12	12:27 — 14:07 F93507 Frontier Airlines Orlando — Atlanta 2h 5m stop 16:18 — 17:18 F92143 Frontier Airlines Atlanta — Chicago	5h 45m including layover	Find flight from$87
13:58 — 14:08 +1 day	13:58 — 15:51 F93469 Frontier Airlines Orlando — Houston 19h 42m stop 11:33 — 14:08 F91882 Frontier Airlines Houston — Chicago	25h 10m including layover	Find flight from$77
14:36 — 22:45	13:58 — 15:51 F93469 Frontier Airlines Orlando — Houston 3h 49m stop 20:21 — 22:52 F93282 Frontier Airlines Houston — Chicago	9h 9m including layover	Find flight from$70
15:34 — 23:29	15:34 — 17:29 F93507 Frontier Airlines Orlando — Atlanta 5h 8m stop 22:28 — 23:29 F92779 Frontier Airlines Atlanta — Chicago	8h 55m including layover	Find flight from$70
15:36 — 22:52	05:36 — 08:08 NK994 Spirit Airlines Orlando — Newark 2h 49m stop 12:08 — 13:44 NK329 Spirit Airlines Newark — Chicago	8h 16m including layover	Find flight from$61
16:54 — 00:12 +2 days	16:54 — 19:15 F91727 Frontier Airlines Orlando — Las Vegas 23h 16m stop 18:31 — 00:12 F92146 Frontier Airlines Las Vegas — Chicago	32h 18m including layover	Find flight from$70
16:54 — 12:34 +1 day	16:54 — 19:15 F91727 Frontier Airlines Orlando — Las Vegas 11h 35m stop 06:50 — 12:34 F92330 Frontier Airlines Las Vegas — Chicago	20h 40m including layover	Find flight from$71
17:00 — 20:49	17:54 — 19:42 F94025 Frontier Airlines Orlando — Atlanta 1h 8m stop 22:58 — 23:55 F92779 Frontier Airlines Atlanta — Chicago	4h 49m including layover	Find flight from$70
19:21 — 00:20 +1 day	19:21 — 21:54 F94170 Frontier Airlines Orlando — Philadelphia 1h 3m stop 22:57 — 00:20 F94367 Frontier Airlines Philadelphia — Chicago	5h 59m including layover	Find flight from$83
19:30 — 11:44 +1 day	08:15 — 10:34 F91875 Frontier Airlines Orlando — Las Vegas 8h 21m stop 06:50 — 12:34 F92330 Frontier Airlines Las Vegas — Chicago	17h 14m including layover	Find flight from$72
20:57 — 17:30 +1 day	20:57 — 23:14 F93311 Frontier Airlines Orlando — Denver 14h 40m stop 13:54 — 17:30 F92048 Frontier Airlines Denver — Chicago	21h 33m including layover	Find flight from$100
20:59 — 15:50 +1 day	20:57 — 23:14 F93311 Frontier Airlines Orlando — Denver 13h 12m stop 12:28 — 15:50 F91228 Frontier Airlines Denver — Chicago	19h 51m including layover	Find flight from$67
21:14 — 14:02 +1 day	20:59 — 23:16 F93311 Frontier Airlines Orlando — Denver 10h 46m stop 20:59 — 00:28 F93172 Frontier Airlines Denver — Chicago	17h 48m including layover	Find flight from$93
21:43 — 11:52 +1 day	20:59 — 23:16 F93311 Frontier Airlines Orlando — Denver 8h 36m stop 08:50 — 12:13 F92210 Frontier Airlines Denver — Chicago	15h 9m including layover	Find flight from$80
22:13 — 12:02 +1 day	22:13 — 23:59 F92452 Frontier Airlines Orlando — Charlotte 10h 41m stop 10:40 — 12:02 F93141 Frontier Airlines Charlotte — Chicago	14h 49m including layover	Find flight from$77
13:15 — 12:04 +1 day	13:15 — 14:55 NK197 Spirit Airlines Orlando — Houston 6h 14m stop 21:09 — 22:30 NK490 Spirit Airlines Houston — Las Vegas 7h 57m stop 06:27 — 12:04 NK187 Spirit Airlines Las Vegas — Chicago	23h 49m including layover	Find flight from$78

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times - local. Updated on May 6, 2025

Flight Information

Below we will explain in detail what the flights cost on the destination from Orlando to Chicago depends on and how to choose the most interesting flight option for you.

Distance between Orlando and Chicago is 1601 miles. Time difference between the cities is 1h. Airplanes depart 05:00 to 22:59 from 3 Orlando airports and arrive 05:00 to 22:59 to 7 Chicago airports. Average flight time is 3h 3m.

The fastest flight 2h 48m
Average flight time 3h 3m
The earliest flight 05:00
The latest flight 22:59
Distance 995 ml

The cheapest months to travel to Chicago are november (from 53 $), december (from 70 $), february (from 70 $).

The most expensive months are january (from 72 $), february (from 70 $), december (from 70 $).

What is the lowest airfare Orlando to Chicago?

The cheapest plane ticket found by our users is $53. This airfare is for economy class on one-way NK316 flight by Spirit Airlines for November 19, 2024 which leaves Orlando Int. in Orlando at 05:00 am and arrives at Chicago O'Hare International at 10:05.

Economy class

$53

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Business class

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First class

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Popular Airlines on the Route

The flight Orlando — Chicago is served by 14 regular airlines and 7 low-cost airlines. Most of the flights on this route are operated by United Airlines - 161 departures per week at the price of from $ 145 . And the most expensive tickets are offered by Delta Air Lines Inc. airline - from $ 1448.

Direct flights

There are 33 nonstop flights on the route. The fastest direct flight is F91457 by Frontier Airlines takes 2h 48m and the cheapest is NK316 by Spirit Airlines for $53.

UA - United Airlines

from $147

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NK - Spirit Airlines

from $95

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F9 - Frontier Airlines

from $53

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AA - American Airlines

from $169

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WN - Southwest Airlines

from $174

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See more direct flights

Connecting Flights

There are 729 flights with layovers on the route. The fastest connecting flight is DL1494 by Delta Air Lines Inc. takes 4h 17m and the cheapest is NK316 by Spirit Airlines for $53.

UA - United Airlines

from $145

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NK - Spirit Airlines

from $53

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AA - American Airlines

from $194

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SY - Sun Country Airlines

from $139

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DL - Delta Air Lines Inc.

from $131

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MX - Mexicana

from $165

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AM - Aeromexico

from $449

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AS - Alaska Airlines

from $258

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F9 - Frontier Airlines

from $67

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B6 - JetBlue

from $610

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WN - Southwest Airlines

from $169

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3M - Gulfstream International Airlines

from $479

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See more connecting flights

Airports

You can fly from Orlando to Chicago from 3 airports (Orlando Int., Herndon, Walt Disney World).

Orlando airports

Orlando Int.-MCO

from $53
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Herndon-ORL

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Walt Disney World-DWS

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Chicago airports

O'Hare International-ORD

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Midway-MDW

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Dupage County-DPA

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Chicago FSS-CHI

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Merrill C Meigs (closed)-CGX

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Pal-Waukee-PWK

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Chicago NAS-NOH

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Airplanes

There are flights to Chicago from Orlando by 14 airlines that use 10 aircraft brands. They range from huge modern airplanes to small-sized.

Boeing 737-100/200

from $102

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Boeing 757-200

from $131

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Aerospatiale/Alenia ATR 72

from $145

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Boeing 737-800

from $169

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Boeing 737 MAX 8

from $174

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Boeing 737 MAX 9

from $184

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Boeing 737-700

from $185

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Airbus A321

from $197

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Airbus A319

from $197

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Boeing 757-300

from $223

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Top Domestic Destinations from Orlando

You may also consider searching for discounted plane tickets to some other popular places from Orlando within United States.

Orlando — New York

from $78

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Orlando — Atlanta

from $72

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Orlando — Miami

from $76

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Orlando — Boston

from $76

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Orlando — Chicago

from $61

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Orlando — Las Vegas

from $63

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Orlando — Houston

from $64

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Orlando — Dallas

from $56

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Orlando — Nashville

from $68

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Orlando — Denver

from $75

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Top International Destinations from Orlando

Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.

Orlando — London

from $59

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Orlando — Toronto

from $69

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Orlando — Cancun

from $61

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Orlando — Paris

from $58

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Orlando — San Juan

from $67

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Orlando — Dublin

from $79

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Orlando — Montreal

from $58

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Orlando — Punta Cana

from $67

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Orlando — Rome

from $70

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Orlando — Vancouver

from $65

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How to book a plane ticket yourself?

Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.
To find a plane ticket, please select dates.