Cheap Flights from CHI to ORL

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The Cheapest Round-trip Tickets from Chicago to Orlando

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26 October 202628 October 2026DirectFrontier AirlinesRT from 111

The Cheapest Flights for this Month from Chicago to Orlando

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17 July 202619 July 2026DirectAllegiant AirRT from 267
21 July 202631 July 20261 StopFrontier AirlinesRT from 270
22 July 202628 July 20261 StopFrontier AirlinesRT from 308
23 July 202629 July 20261 StopFrontier AirlinesRT from 287
29 July 20262 August 20261 StopAllegiant AirRT from 263
5 August 202610 August 2026DirectFrontier AirlinesRT from 192
6 August 202610 August 2026DirectFrontier AirlinesRT from 165
7 August 202610 August 2026DirectAllegiant AirRT from 181
13 August 202617 August 2026DirectFrontier AirlinesRT from 125
18 August 202618 August 20261 StopFrontier AirlinesRT from 170
22 August 202631 August 2026DirectFrontier AirlinesRT from 140
23 August 202624 August 20261 StopAllegiant AirRT from 180
26 August 202631 August 2026DirectFrontier AirlinesRT from 137
28 August 202630 August 20261 StopFrontier AirlinesRT from 145
26 September 20261 October 2026DirectFrontier AirlinesRT from 138
27 September 20262 October 2026DirectFrontier AirlinesRT from 213
26 October 202628 October 2026DirectFrontier AirlinesRT from 111
27 October 20264 November 2026DirectFrontier AirlinesRT from 138
31 October 20264 November 2026DirectSouthwest AirlinesRT from 181
5 November 202610 November 20261 StopSouthwest AirlinesRT from 213
12 November 202616 November 2026DirectFrontier AirlinesRT from 149
13 November 202616 November 2026DirectAllegiant AirRT from 221
6 January 202712 January 2027DirectSouthwest AirlinesRT from 320
7 January 202712 January 2027DirectSouthwest AirlinesRT from 343
24 January 202727 January 2027DirectSouthwest AirlinesRT from 343
25 January 202727 January 20272 StopsAllegiant AirRT from 333
1 April 20274 April 2027DirectAmerican AirlinesRT from 458

The Cheapest Flights from Chicago to Orlando for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
29 July 20262 August 20261 StopAllegiant AirRT from 263
13 August 202617 August 2026DirectFrontier AirlinesRT from 125
26 September 20261 October 2026DirectFrontier AirlinesRT from 138
26 October 202628 October 2026DirectFrontier AirlinesRT from 111
12 November 202616 November 2026DirectFrontier AirlinesRT from 149
6 January 202712 January 2027DirectSouthwest AirlinesRT from 320
1 April 20274 April 2027DirectAmerican AirlinesRT from 458
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