Flights from Illinois (Illinois) to Florida (Florida)

Change search
Chicago (MDW) to Orlando (MCO)
 Depart 28 May 14
 Return 04 Jun 14

Flying with AirTran Airways

Price subject to availability

   View more dates
 
  • Price
  • Dep date
  15 more Flightnetwork flights available on this route
$294   Dep 21 May 14 - Rtn 28 May 14
Chicago to Orlando
MDW to MCO Flightnetwork
$313   Dep 21 May 14 - Rtn 28 May 14
Chicago to Orlando
ORD to MCO Flightnetwork
$314   Dep 28 May 14 - Rtn 04 Jun 14
Chicago to Orlando
ORD to MCO Flightnetwork
$319   Dep 28 May 14 - Rtn 04 Jun 14
Chicago to Fort Myers
MDW to RSW Flightnetwork
$321   Dep 28 May 14 - Rtn 04 Jun 14
Chicago to Fort Myers
ORD to RSW Flightnetwork
$328   Dep 28 May 14 - Rtn 04 Jun 14
Chicago to Tampa
MDW to TPA Flightnetwork
$331   Dep 21 May 14 - Rtn 28 May 14
Chicago to Tampa
ORD to TPA Flightnetwork
$331   Dep 21 May 14 - Rtn 28 May 14
Chicago to Fort Lauderdale
MDW to FLL Flightnetwork
$331   Dep 28 May 14 - Rtn 04 Jun 14
Chicago to Fort Lauderdale
MDW to FLL Flightnetwork
$332   Dep 21 May 14 - Rtn 28 May 14
Chicago to Fort Myers
MDW to RSW Flightnetwork
$332   Dep 28 May 14 - Rtn 04 Jun 14
Chicago to Tampa
MDW to TPA Flightnetwork
$333   Dep 28 May 14 - Rtn 04 Jun 14
Chicago to Fort Myers
MDW to RSW Flightnetwork
$344   Dep 21 May 14 - Rtn 28 May 14
Chicago to Tampa
MDW to TPA Flightnetwork
$347   Dep 21 May 14 - Rtn 28 May 14
Chicago to Fort Myers
MDW to RSW Flightnetwork
$349   Dep 21 May 14 - Rtn 28 May 14
Chicago to Miami International
MDW to MIA Flightnetwork
Chicago (ORD) to Orlando (MCO)
 Depart 14 May 14
 Return 21 May 14

Flying with Spirit Airlines

Price subject to availability

   View more dates
 
  • Price
  • Dep date
  15 more Expedia flights available on this route
$204   Dep 21 May 14 - Rtn 28 May 14
Chicago to Orlando
ORD to MCO Expedia
$240   Dep 25 Jun 14 - Rtn 02 Jul 14
Chicago to Orlando
ORD to MCO Expedia
$258   Dep 14 May 14 - Rtn 21 May 14
Chicago to Orlando
MDW to MCO Expedia
$258   Dep 21 May 14 - Rtn 28 May 14
Chicago to Orlando
MDW to MCO Expedia
$268   Dep 25 Jun 14 - Rtn 02 Jul 14
Chicago to Tampa
ORD to TPA Expedia
$269   Dep 25 Jun 14 - Rtn 02 Jul 14
Chicago to Orlando
MDW to MCO Expedia
$287   Dep 25 Jun 14 - Rtn 02 Jul 14
Chicago to Fort Myers
MDW to RSW Expedia
$288   Dep 21 May 14 - Rtn 28 May 14
Chicago to Tampa
ORD to TPA Expedia
$292   Dep 21 May 14 - Rtn 28 May 14
Chicago to Tampa
MDW to TPA Expedia
$294   Dep 14 May 14 - Rtn 21 May 14
Chicago to Fort Myers
MDW to RSW Expedia
$308   Dep 14 May 14 - Rtn 21 May 14
Chicago to Fort Lauderdale
ORD to FLL Expedia
$308   Dep 21 May 14 - Rtn 28 May 14
Chicago to Fort Lauderdale
ORD to FLL Expedia
$308   Dep 25 Jun 14 - Rtn 02 Jul 14
Chicago to Fort Lauderdale
ORD to FLL Expedia
$311   Dep 21 May 14 - Rtn 28 May 14
Chicago to Fort Myers
MDW to RSW Expedia
$316   Dep 14 May 14 - Rtn 21 May 14
Chicago to Jacksonville
MDW to JAX Expedia
Chicago (CHI) to Orlando (ORL)
 Depart 18 May 14
 Return 22 May 14

Price subject to availability

   View more dates
 
  • Price
  • Dep date
  5 more OneTravel.com flights available on this route
$279   Dep 16 May 14 - Rtn 23 May 14
Chicago to Orlando
ORD to MCO OneTravel.com
$301   Dep 18 May 14 - Rtn 22 May 14
Chicago to Miami International
ORD to MIA OneTravel.com
$323   Dep 16 May 14 - Rtn 23 May 14
Chicago to Tampa
ORD to TPA OneTravel.com
$339   Dep 16 May 14 - Rtn 23 May 14
Chicago to Fort Myers
ORD to RSW OneTravel.com
$389   Dep 16 May 14 - Rtn 23 May 14
Chicago to Fort Lauderdale
ORD to FLL OneTravel.com
Chicago (MDW) to Fort Myers (RSW)
 Depart 22 May 14
 Return 29 May 14

Price subject to availability

   View more dates
 
  • Price
  • Dep date
  7 more CheapOair.com flights available on this route
$275   Dep 22 May 14 - Rtn 29 May 14
Chicago to Orlando
MDW to MCO CheapOair.com
$288   Dep 22 May 14 - Rtn 29 May 14
Chicago to Sarasota
ORD to SRQ CheapOair.com
$312   Dep 22 May 14 - Rtn 29 May 14
Chicago to Jacksonville
MDW to JAX CheapOair.com
$318   Dep 22 May 14 - Rtn 29 May 14
Chicago to Tampa
ORD to TPA CheapOair.com
$333   Dep 22 May 14 - Rtn 29 May 14
Chicago to Fort Lauderdale
CHI to FLL CheapOair.com
$383   Dep 22 May 14 - Rtn 29 May 14
Chicago to Miami International
ORD to MIA CheapOair.com
$436   Dep 22 May 14 - Rtn 29 May 14
Chicago to West Palm Beach
ORD to PBI CheapOair.com
Chicago (CHI) to Orlando (ORL)
 Depart 14 May 14
 Return 21 May 14

Price subject to availability

   View more dates
 
Chicago (ORD) to Orlando (MCO)
 Depart 02 Jul 14
 Return 09 Jul 14

Flying with Spirit Airlines

Price subject to availability

   View more dates
 
  • Price
  • Dep date
  15 more momondo.com flights available on this route
$248   Dep 09 Jul 14 - Rtn 16 Jul 14
Chicago to Orlando
ORD to MCO momondo.com
$248   Dep 16 Jul 14 - Rtn 23 Jul 14
Chicago to Orlando
ORD to MCO momondo.com
$248   Dep 23 Jul 14 - Rtn 30 Jul 14
Chicago to Orlando
ORD to MCO momondo.com
$258   Dep 25 Jun 14 - Rtn 02 Jul 14
Chicago to Orlando
MDW to MCO momondo.com
$258   Dep 02 Jul 14 - Rtn 09 Jul 14
Chicago to Orlando
MDW to MCO momondo.com
$258   Dep 23 Jul 14 - Rtn 30 Jul 14
Chicago to Orlando
MDW to MCO momondo.com
$268   Dep 09 Jul 14 - Rtn 16 Jul 14
Chicago to Orlando
MDW to MCO momondo.com
$276   Dep 09 Jul 14 - Rtn 16 Jul 14
Chicago to Fort Myers
ORD to RSW momondo.com
$276   Dep 16 Jul 14 - Rtn 23 Jul 14
Chicago to Fort Myers
ORD to RSW momondo.com
$276   Dep 16 Jul 14 - Rtn 23 Jul 14
Chicago to Fort Myers
MDW to RSW momondo.com
$276   Dep 23 Jul 14 - Rtn 30 Jul 14
Chicago to Fort Myers
MDW to RSW momondo.com
$278   Dep 25 Jun 14 - Rtn 02 Jul 14
Chicago to Fort Lauderdale
ORD to FLL momondo.com
$278   Dep 16 Jul 14 - Rtn 23 Jul 14
Chicago to Orlando
MDW to MCO momondo.com
$282   Dep 09 Jul 14 - Rtn 16 Jul 14
Chicago to Fort Lauderdale
ORD to FLL momondo.com
$286   Dep 02 Jul 14 - Rtn 09 Jul 14
Chicago to Fort Myers
ORD to RSW momondo.com
Chicago (ORD) to Orlando (ORL)
 Depart 06 May 14
 Return 13 May 14

Flying with Spirit Airlines

Price subject to availability

   View more dates
 
FlightsTo
Search recommended websites
  • Recent Searches
From placeholder To placeholder
Staying in placeholder
Pick up placeholder
Thank you for subscribing to the Cheapflights newsletter
Searching... Find deals  
GO  
  • Clear recent searches
  • Enter your travel details and click ‘Find deals’ to see a list of partners with great airfare offers to your destination

    Sorry, we do not have any partners that match your search criteria.