Cheapest flights from Chicago to anywhere, anytime from $36

Cheapest flight deals per destination from Chicago (MDW)  from $36

Cheapest flight destinations from Chicago in the next 12 months. Click a price to see the available cheapest deals for each month.

Return flights

Aguadilla (BQN)
Atlanta (ATL) direct
Beirut (BEY)
Belize City (BZE)
Bogota (BOG)
Cairo (CAI)
Cancun (CUN) direct
Cancun (CUN)
Caracas (CCS)
Dhaka (DAC)
Dublin (DUB)
Guangzhou (CAN)
Jeddah (JED)
Kathmandu (KTM)
Keflavik (KEF)
Lagos (LOS)
Lima (LIM)
Ljubljana (LJU)
Managua (MGA)
Montego Bay (MBJ)
Philipsburg (SXM)
Pointe-a-pitre (PTP)
Punta Cana (PUJ)
Seoul (ICN)
Sofia (SOF)

Also check the deals for one-way flights from Chicago.


The deals are updated by AirHint regularly. Please keep in mind that the price may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Book now to secure these cheap prices.