Cheapest Flights From Chicago

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Here’s the cheapest flights from Chicago across all of the USA. There’s cheap flights to Baltimore, Las Vegas, New York, Miami, Seattle, San Francisco and loads more. If you don’t see your destination or if you prefer to search your own flights, click any flight and adjust the cities and dates, or search any flight here ✈️.

The key is flexibility – don’t expect flight sales on a weekend in the school holidays. Do expect cheap flights midweek, when the weather is extreme and there’s few other tourists or no events on.

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Here’s the cheapest flights from Chicago for the next few months.

Origin - DestinationDeparture atReturn atPriceFind tickets
Chicago ↔ Miami1 June 20224 June 2022 174 174
Chicago ↔ New York3 March 20237 March 2023 186 186
Chicago ↔ Boston29 May 202230 May 2022 191 191
Chicago ↔ Fort Lauderdale7 June 202210 June 2022 220 220
Chicago ↔ Las Vegas26 August 202229 August 2022 272 272
Chicago ↔ Cleveland3 June 20225 June 2022 299 299
Chicago ↔ Orlando11 June 202212 June 2022 306 306
Chicago ↔ Baltimore1 June 20225 June 2022 320 320
Chicago ↔ Atlanta29 May 202231 May 2022 320 320
Chicago ↔ Washington1 June 20225 June 2022 324 324
Chicago ↔ Dallas7 June 20229 June 2022 340 340
Chicago ↔ Mexico City4 June 20228 June 2022 350 350
Chicago ↔ Devils Lake23 August 202226 August 2022 354 354
Chicago ↔ Seattle23 August 202226 August 2022 391 391
Chicago ↔ Lansing15 June 202216 June 2022 408 408
Chicago ↔ Merida28 May 20221 June 2022 473 473
Chicago ↔ Nassau29 July 202231 July 2022 600 600
Chicago ↔ Spokane9 July 202212 July 2022 655 655
Chicago ↔ Portland6 June 20229 June 2022 682 682
Chicago ↔ Tallinn22 July 202224 July 2022 703 703
Chicago ↔ McAllen28 May 202230 May 2022 752 752
Chicago ↔ Ontario28 May 202230 May 2022 818 818
Chicago ↔ Cayo Coco29 July 202230 July 2022 927 927
Chicago ↔ North Eleuthera29 July 202231 July 2022 944 944
Chicago ↔ Moscow17 September 202219 September 2022 1 205 1 205
Chicago ↔ Istanbul27 May 20221 June 2022 1 213 1 213
Chicago ↔ Tbilisi24 June 202230 June 2022 1 374 1 374
Chicago ↔ Tashkent9 June 202212 June 2022 2 460 2 460
Chicago ↔ Hong Kong1 June 20222 June 2022 2 713 2 713
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If you didn’t see any destination you liked, then search all flights here ✈️.

All prices are based on previous searches. If you click through and the cheap price is no longer visible, it means the flight has been booked out. Try searching alternative dates. Have questions? just ask. Cheap flights may not be available on all days or across all airlines. Restrictions may apply including a ticket being non-refundable or with limited baggage. Always read the terms and conditions and keep a copy for reference. You can view our terms here.


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The Flight Sale Team.

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