A good sale to Florianopolis Matrix Airfare Search by ITA Software will price this at $507 (Basic Economy). Use those dates on Read More
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Chicago
chicago flight deals
Cathay Pacific: Chicago – Singapore. $749. Roundtrip, including all Taxes
A good sale to Singapore Sample Travel Date: January 22nd – 29th, 2026 This is just ONE SAMPLE travel date, for more Read More
American: Chicago – San Diego (and vice versa). $153 (Basic Economy) / $243 (Regular Economy). Roundtrip, including all Taxes
A good sale to/from San Diego Matrix Airfare Search by ITA Software will price this at $243 (Regular Economy). Use those dates Read More
United: Chicago – Barcelona, Spain. $419 (Basic Economy) / $619 (Regular Economy). Roundtrip, including all Taxes
A good sale to Barcelona. United and its partners Air Canada, Austrian, Lufthansa and Swiss Air’s $619 fare is a regular economy Read More
Copa: Chicago – Sao Paulo, Brazil. $387 (Basic Economy) / $567 (Regular Economy). Roundtrip, including all Taxes
A good sale to Sao Paulo Matrix Airfare Search by ITA Software will price this at $436 (Basic Economy). Use those dates Read More
United: Chicago – Sao Paulo, Brazil. $435 (Basic Economy) / $615 (Regular Economy). Roundtrip, including all Taxes
A good sale to Sao Paulo United’s $615 fare is a regular economy fare with ONE checked bag and a normal size Read More
American: Chicago – Guatemala City, Guatemala. $196 (Basic Economy) / $256 (Regular Economy). Roundtrip, including all Taxes
A good sale to Guatemala City Matrix Airfare Search by ITA Software will price this at $256 (Regular Economy). Use those dates Read More
United: Chicago – San Juan, Puerto Rico. $218 (Basic Economy) / $308 (Regular Economy). Roundtrip, including all Taxes
A good sale to San Juan. Matrix Airfare Search by ITA Software will price this at $308 (Regular Economy). Use those dates Read More
United: Los Angeles – Chicago (and vice versa). $165 (Basic Economy) / $255 (Regular Economy). Roundtrip, including all Taxes
A good sale for nonstop service to/from Chicago Matrix Airfare Search by ITA Software will price this at $255 (Regular Economy). Use Read More
United: Chicago – Las Vegas, Nevada (and vice versa). $159 (Basic Economy) / $249 (Regular Economy). Roundtrip, including all Taxes
A good sale for to/from Las Vegas Matrix Airfare Search by ITA Software will price this at $249 (Regular Economy). Use those Read More
United: Portland – Chicago (and vice versa). $165 (Basic Economy) / $255 (Regular Economy). Roundtrip, including all Taxes
A good sale for to/from Chicago Matrix Airfare Search by ITA Software will price this at $255 (Regular Economy). Use those dates Read More
United: Chicago – Palm Springs, California (and vice versa). $163 (Basic Economy) / $253 (Regular Economy). Roundtrip, including all Taxes
A good sale to / from Palm Springs. Matrix Airfare Search by ITA Software will price this at $253 (Regular Economy). Use Read More
American: Phoenix – Chicago (and vice versa). $149 (Basic Economy) / $229 (Regular Economy). Roundtrip, including all Taxes
A good sale to/from Chicago. Matrix Airfare Search by ITA Software will price this at $229 (Regular Economy). Use those dates on Read More
United: San Francisco – Chicago (and vice versa). $165 (Basic Economy) / $255 (Regular Economy). Roundtrip, including all Taxes
A good sale to / from Chicago Matrix Airfare Search by ITA Software will price this at $255 (Regular Economy). Use those Read More
American: Chicago – Maui, Hawaii (and vice versa). $361 (Basic Economy) / $501 (Regular Economy). Roundtrip, including all Taxes
A good sale to/from Maui Matrix Airfare Search by ITA Software will price this at $501 (Regular Economy). Use those dates on Read More
Korean Air: Chicago – Bangkok, Thailand. $698. Roundtrip, including all Taxes
A good sale to Bangkok Sample Travel Date: November 10th – 17th This is just ONE SAMPLE travel date, for more availability, Read More
Iberia: Chicago – Madrid, Spain. $423 (Basic Economy) / $623 (Regular Economy). Roundtrip, including all Taxes
A good sale to Madrid Matrix Airfare Search by ITA Software will price this at $651 (Regular Economy). Use those dates on Read More
Iberia: Chicago – Bilbao, Spain. $469 (Basic Economy) / $669 (Regular Economy). Roundtrip, including all Taxes
A good sale to Bilbao Matrix Airfare Search by ITA Software will price this at $697 (Regular Economy). Use those dates on Read More