A good sale to Malta. Pricing will vary slightly depending on routing. Matrix Airfare Search by ITA Software will price this $556 Read More
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Chicago
chicago flight deals
United: Chicago – San Diego (and vice versa). $157 (Basic Economy) / $247 (Regular Economy). Roundtrip, including all Taxes
A good sale for nonstop service to/from San Diego Matrix Airfare Search by ITA Software will price this at $247 (Regular Economy). Read More
jetBlue: Chicago – San Juan, Puerto Rico. $149 (Basic Economy) / $239 (Regular Economy). Roundtrip, including all Taxes
A good sale for nonstop service to San Juan The $239 fare is a regular economy fare that allows for normal size Read More
Copa: Chicago – Bogota, Colombia. $309 (Basic Economy / $419 (Regular Economy). Roundtrip, including all Taxes
A good sale to Bogota Matrix Airfare Search by ITA Software will price this at $357 (Basic Economy). Use those dates on Read More
Korean Air: Chicago – Singapore. $858. Roundtrip, including all Taxes
A good sale to Singapore Sample Travel Date: February 18th – 25th, 2026 This is just ONE SAMPLE travel date, for more Read More
American: Chicago – Auckland, New Zealand. $861 (Basic Economy) / $1,061 (Regular Economy). Roundtrip, including all Taxes
A good sale to Auckland Matrix Airfare Search by ITA Software will price this at $1,061 (Regular Economy). Use those dates on Read More
American: Chicago – Honolulu, Hawaii (and vice versa). $403 (Basic Economy) / $543 (Regular Economy). Roundtrip, including all Taxes
A good sale for nonstop service to / from Honolulu. Matrix Airfare Search by ITA Software will price this at $543 (Regular Read More
American: Chicago – Kona, Hawaii (and vice versa). $421 (Basic Economy) / $561 (Regular Economy). Roundtrip, including all Taxes
A good sale to / from Kona. Pricing will vary slightly depending on routing Matrix Airfare Search by ITA Software will price Read More
Iberia: Chicago – Madrid, Spain. $473 (Basic Economy) / $673 (Regular Economy). Roundtrip, including all Taxes
A good sale to Madrid Matrix Airfare Search by ITA Software will price this at $701 (Regular Economy). Use those dates on Read More
Scandinavian Airlines: Chicago – Vienna, Austria. $474 (Basic Economy) / $574 (Regular Economy). Roundtrip, including all Taxes
A good sale to Vienna Matrix Airfare Search by ITA Software will price this at $486 (Basic Economy). Use those dates on Read More
United: Chicago – Dubai, United Arab Emirates. $677. Roundtrip, including all Taxes
A good sale to Dubai. Sample Travel Date: January 21st – 28th, 2026 This is just ONE SAMPLE travel date, for more Read More
American: Chicago – Kauai, Hawaii (and vice versa). $423 (Basic Economy) / $563 (Regular Economy). Roundtrip, including all Taxes
A good sale to / from Kauai. Pricing will vary slightly depending on routing Matrix Airfare Search by ITA Software will price Read More
United: Chicago – Guatemala City, Guatemala. $211 (Basic Economy) / $321 (Regular Economy). Roundtrip, including all Taxes
A good sale to Guatemala City Matrix Airfare Search by ITA Software will price this at $321 (Regular Economy). Use those dates Read More
United: Chicago – Taipei, Taiwan. $749 (Basic Economy) / $919 (Regular Economy). Roundtrip, including all Taxes
A good sale to Taipei United’s $919 fare is a regular economy fare with TWO checked bags , normal size carry-on and Read More
American: Chicago – Rio de Janeiro, Brazil. $500 (Basic Economy) / $620 (Regular Economy). Roundtrip, including all Taxes
A good sale to Rio de Janeiro. Matrix Airfare Search by ITA Software will price this at $620 (Regular Economy). Use those Read More
Korean Air: Chicago – Bali, Indonesia. $863. Roundtrip, including all Taxes
A good sale to Bali Sample Travel Date: April 1st – 8th, 2026 This is just ONE SAMPLE travel date, for more Read More
Copa Air: Chicago – Medellin, Colombia. $287 (Basic Economy) / $407 (Regular Economy). Roundtrip, including all Taxes
A good sale to Medellin Matrix Airfare Search by ITA Software will price this at $335 (Basic Economy). Use those dates on Read More
Copa: Chicago – Cartagena, Colombia. $290 (Basic Economy / $390 (Regular Economy). Roundtrip, including all Taxes
A good sale to Cartagena Matrix Airfare Search by ITA Software will price this at $338 (Basic Economy). Use those dates on Read More