- San Francisco (SFO) Chicago Midway (MDW)
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1 non-stop flight per dayat least 4hfrom $167 - Boston (BOS) Chicago Midway (MDW)
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3–7 non-stop flights per dayat least 2h 30minfrom $172 - Los Angeles (LAX) Chicago Midway (MDW)
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3–6 non-stop flights per dayat least 3hfrom $185 - Orlando (MCO) Chicago Midway (MDW)
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6–10 non-stop flights per dayat least 2h 40minfrom $197 - Atlanta (ATL) Chicago Midway (MDW)
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7–17 non-stop flights per dayat least 1h 45minfrom $86 - Washington DC (DCA) Chicago Midway (MDW)
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4–8 non-stop flights per dayat least 1h 50minfrom $216 - Tampa (TPA) Chicago Midway (MDW)
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3–8 non-stop flights per dayat least 2h 35minfrom $235 - Minneapolis (MSP) Chicago Midway (MDW)
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4–13 non-stop flights per dayat least 1h 25minfrom $229 - Newark (EWR) Chicago Midway (MDW)
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only flights with stopoverat least 9h 15minfrom $244