Cheapest flights from Chicago to anywhere, anytime from $215

Cheapest flight deals per destination from Chicago (MDW) from $215

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

Return flights

Abu Dhabi (AUH)
Algier (ALG)
Amman (AMM)
Amsterdam (AMS)
Athens (ATH)
Bangkok (BKK)
Belgrade (BEG)
Belize City (BZE)
Bogota (BOG)
Brussels (BRU)
Buenos Aires (EZE)
Cairo (CAI)
Cape Town (CPT)
Casablanca (CMN)
Cluj-napoca (CLJ)
Denpasar (DPS)
Doha (DOH)
Dublin (DUB)
Frankfurt (FRA)
Gothenborg (GOT)
Guadalajara (GDL) direct
Guatemala City (GUA)
Helsinki (HEL)
Hyderabad (HYD)
Istanbul (SAW)
Keflavik (KEF)
Krakow (KRK)
Kuala Lumpur (KUL)
Lagos (LOS)
Lima (LIM)
Lisbon (LIS)
London (LGW)
Madrid (MAD)
Manila (MNL)
Milano (MXP)
Montego Bay (MBJ)
Nassau (NAS)
Oslo (OSL)
Palanga (PLQ)
Panama City (PTY)
Paris (CDG)
Prague (PRG)
Pristina (PRN)
Punta Cana (PUJ)
Quito (UIO)
San Jose (SJO)
San Juan (SJU)
San Salvador (SAL)
Santiago (SCL)
Sao Paulo (GRU)
Seoul (ICN)
Shanghai (PVG)
Singapore (SIN)
Skopje (SKP)
Sofia (SOF)
Sydney (SYD)
Taipei (TPE)
Tehran (IKA)
Tel Aviv (TLV)
Tirana (TIA)
Tokyo (NRT)
Toronto (YTZ) direct
Tunis (TUN)
Vienna (VIE)
Zagreb (ZAG)
Zurich (ZRH)

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

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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.