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

Accra (ACC)
Agadir (AGA)
Amman (AMM)
Amsterdam (AMS)
Auckland (AKL)
Belize City (BZE)
Bogota (BOG)
Brussels (BRU)
Bucharest (OTP)
Budapest (BUD)
Buenos Aires (EZE)
Cancun (CUN)
Caracas (CCS)
Cheju (CJU)
Copenhagen (CPH)
Dubai (DXB)
Dublin (DUB)
Geneva (GVA)
Guatemala City (GUA)
Istanbul (SAW)
Keflavik (KEF)
Kuala Lumpur (KUL)
Lagos (LOS)
Ljubljana (LJU)
Madrid (MAD)
Manila (MNL)
Miami (MIA) direct
Mumbai (BOM)
Nairobi (NBO)
Panama City (PTY)
Paris (CDG)
Podgorica (TGD)
Punta Cana (PUJ)
Quito (UIO)
Rome (FCO)
San Juan (SJU)
San Pedro Sula (SAP)
San Salvador (SAL)
Sao Paulo (GRU)
Sarajevo (SJJ)
Shanghai (PVG)
Singapore (SIN)
Skopje (SKP)
Taipei (TPE)
Tallinn (TLL)
Tashkent (TAS)
Tel Aviv (TLV)
Tirana (TIA)
Tokyo (HND)
Toronto (YTZ) direct
Vienna (VIE)
Vilnius (VNO)
Warsaw (WAW)
Zagreb (ZAG)

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.