Cheapest flights from Chicago to anywhere, anytime from $72

Cheapest flight deals per destination from Chicago (MDW)  from $72

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

Amman (AMM)
Amsterdam (AMS)
Bangkok (BKK)
Barcelona (BCN)
Belize City (BZE)
Belo Horizonte (CNF)
Cancun (CUN) direct
Cape Town (CPT)
Denpasar (DPS)
Dublin (DUB)
Ljubljana (LJU)
London (LGW)
Malta (MLA)
Manila (MNL)
Marrakech (RAK)
Montevideo (MVD)
Nairobi (NBO)
Oranjestad (AUA)
Papeete (PPT)
Paris (CDG)
Philipsburg (SXM)
Port-of-spain (POS)
Prague (PRG)
San Juan (SJU)
Singapore (SIN)
Sofia (SOF)
Tallinn (TLL)
Tbilisi (TBS)
Tokyo (NRT)
Toronto (YTZ) direct
Tunis (TUN)
Warsaw (WAW)

Also check the deals for return 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.