Cheapest flights from Chicago to anywhere, anytime from $58

Cheapest flight deals per destination from Chicago (MDW) from $58

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

One-Way flights

Algier (ALG)
Auckland (AKL)
Baghdad (BGW)
Barcelona (BCN)
Brasilia (BSB)
Brussels (BRU)
Cartagena (CTG)
Chisinau (RMO)
Delhi (DEL)
Dhaka (DAC)
Ho Chi Minh City (SGN)
Istanbul (IST)
Lahore (LHE)
Lima (LIM)
London (LGW)
Montego Bay (MBJ) direct
Monterrey (MTY)
Nairobi (NBO)
Nassau (NAS)
Philipsburg (SXM)
Prague (PRG)
Punta Cana (PUJ) direct
Riga (RIX)
San Juan (SJU)
San Juan (SJU) direct
Sarajevo (SJJ)
Tbilisi (TBS)
Tokyo (NRT)
Toronto (YTZ) direct
Willemstad (CUR)

Also check the deals for return flights from Chicago.

Skyscanner

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.