Our cheapest offers for flights to Chicago Midway

Here you can compare cheap flights to Chicago Midway (MDW) for either one-way or return trips. The following offers for Chicago Midway were found on our flight search in the last days. Prices may vary depending on the flight route, date and availability.

Flights from San Francisco (SFO) to Chicago Midway (MDW)

	Outbound	Return	Airlines	Baggage	Price
San Francisco Chicago Midway	Outbound 04/12/25 1 Stopover (LAS) F92486, F92330 28h 21min	Return 04/27/25 1 Stopover (DEN) F92209, F93439 06h 32min	Frontier Airlines		$220
San Francisco Chicago Midway	Outbound 04/12/25 2 Stopovers (LAX, DEN) F93308, F93156, F92210 30h 51min	Return 04/27/25 2 Stopovers (ATL, PHX) F92292, F91099, F91191 25h 19min	Frontier Airlines	?	$283
San Francisco Chicago Midway	Outbound 04/12/25 1 Stopover (LAS) F92486, F92330 28h 21min	Return 04/27/25 1 Stopover (DEN) F92209, F93439 06h 32min	Frontier Airlines		$224

Flights from Atlanta (ATL) to Chicago Midway (MDW)

	Outbound	Return	Airlines	Baggage	Price
Best option Atlanta Chicago Midway	Outbound 04/21/25 direct F92143 02h 03min	Return 05/19/25 direct F92292 02h 12min	Frontier Airlines	?	$75
Atlanta Chicago Midway	Outbound 04/21/25 direct F92143 02h 03min	Return 05/19/25 direct F92292 02h 12min	Frontier Airlines	?	$78
Atlanta Chicago Midway	Outbound 04/21/25 direct F92143 02h 03min	Return 05/19/25 direct F92292 02h 12min	Frontier Airlines		$76

Flights from Boston (BOS) to Chicago Midway (MDW)

	Outbound	Return	Airlines	Baggage	Price
Boston Chicago Midway	Outbound 06/08/25 1 Stopover (TPA) F91215, F93899 13h 36min	Return 06/12/25 1 Stopover (MCO) F93854, F93348 27h 00min	Frontier Airlines		$240
Boston Chicago Midway	Outbound 06/08/25 1 Stopover (TPA) F91215, F93899 13h 36min	Return 06/12/25 1 Stopover (MCO) F93854, F93348 27h 00min	Frontier Airlines		$250
Boston Chicago Midway	Outbound 04/12/25 1 Stopover (ATL) F93511, F92779 17h 16min	Return 04/27/25 1 Stopover (ATL) F92292, F93512 18h 13min	Frontier Airlines	?	$247

Flights from Washington DC (DCA) to Chicago Midway (MDW)

	Outbound	Return	Airlines	Baggage	Price
Best option Washington DC Chicago Midway	Outbound 06/18/25 1 Stopover (ATL) DL0410, DL1063 04h 54min	Return 07/15/25 1 Stopover (DTW) DL3501, DL2073 03h 53min	Delta Air Lines	?	$222
Washington DC Chicago Midway	Outbound 04/21/25 3 Stopovers (DEN, ATL, IAH) F90685, F93294, F92399, F93282 57h 13min	Return 05/19/25 2 Stopovers (ATL, DEN) F92144, F91449, F90686 26h 37min	Frontier Airlines	?	$314
Washington DC Chicago Midway	Outbound 04/21/25 1 Stopover (DEN) F90689, F92210 07h 21min	Return 05/19/25 1 Stopover (DEN) F92209, F90686 15h 04min	Frontier Airlines	?	$227

Flights from Newark (EWR) to Chicago Midway (MDW)

	Outbound	Return	Airlines	Baggage	Price
Best option Newark Chicago Midway	Outbound 04/21/25 1 Stopover (ATL) F94601, F92143 12h 16min	Return 05/19/25 1 Stopover (ATL) F92144, F94602 11h 36min	Frontier Airlines		$112
Newark Chicago Midway	Outbound 04/21/25 1 Stopover (ATL) F94601, F92143 12h 16min	Return 05/19/25 1 Stopover (ATL) F92292, F94602 25h 28min	Frontier Airlines	?	$143
Newark Chicago Midway	Outbound 04/21/25 1 Stopover (ATL) F94601, F92143 12h 16min	Return 05/19/25 1 Stopover (ATL) F92144, F94602 11h 36min	Frontier Airlines		$116

Flights from Los Angeles (LAX) to Chicago Midway (MDW)

	Outbound	Return	Airlines	Baggage	Price
Los Angeles Chicago Midway	Outbound 04/12/25 1 Stopover (DEN) F92342, F92210 07h 46min	Return 04/27/25 1 Stopover (LAS) F92329, F91183 28h 20min	Frontier Airlines		$210
Los Angeles Chicago Midway	Outbound 04/12/25 1 Stopover (DEN) F92342, F92210 07h 46min	Return 04/27/25 2 Stopovers (YTZ, YYZ, YVR) PD2388, WS0711, WS1698 35h 08min	Frontier Airlines	?	$399
Best option Los Angeles Chicago Midway	Outbound 06/18/25 direct WN2773 04h 00min	Return 07/15/25 1 Stopover (MSP) DL3778, DL2327 07h 37min	Southwest Airlines	?	$263

Flights from Orlando (MCO) to Chicago Midway (MDW)

	Outbound	Return	Airlines	Baggage	Price
Best option Orlando Chicago Midway	Outbound 04/12/25 direct F91457 03h 01min	Return 04/27/25 direct F93854 02h 51min	Frontier Airlines		$204
Orlando Chicago Midway	Outbound 04/12/25 1 Stopover (ATL) F91563, F92779 17h 51min	Return 04/27/25 1 Stopover (ATL) F92292, F93508 27h 38min	Frontier Airlines	?	$206
Orlando Chicago Midway	Outbound 06/18/25 1 Stopover (ATL) DL1494, DL1063 04h 39min	Return 07/15/25 1 Stopover (ATL) DL2307, DL1735 05h 06min	Delta Air Lines	?	$204

Flights from Minneapolis (MSP) to Chicago Midway (MDW)

	Outbound	Return	Airlines	Baggage	Price
Best option Minneapolis Chicago Midway	Outbound 06/18/25 direct WN2576 01h 30min	Return 07/15/25 direct DL3795 01h 35min	Southwest Airlines	?	$229
Minneapolis Chicago Midway Pay attention to transfer at connecting flight	Outbound 04/12/25 1 Stopover (VPS) G43112, G43100 27h 47min	Return 04/27/25 2 Stopovers (PGD, BNA) G40944, G40847, SY0634 34h 37min	Allegiant Air		$590
Minneapolis Chicago Midway	Outbound 04/12/25 1 Stopover (ATL) SY0355, F92779 15h 14min	Return 04/27/25 1 Stopover (ATL) F92292, SY0356 21h 36min	Sun Country Airlines, Frontier Airlines	?	$325

Flights from Tampa (TPA) to Chicago Midway (MDW)

	Outbound	Return	Airlines	Baggage	Price
Best option Tampa Chicago Midway	Outbound 04/12/25 direct F93899 02h 51min	Return 04/27/25 direct F91186 02h 40min	Frontier Airlines	?	$134
Tampa Chicago Midway	Outbound 04/12/25 direct F93899 02h 51min	Return 04/27/25 direct F91186 02h 40min	Frontier Airlines		$139
Tampa Chicago Midway	Outbound 04/12/25 direct F93899 02h 51min	Return 04/27/25 direct F91186 02h 40min	Frontier Airlines		$137