- San Francisco (SFO) Chicago Midway (MDW)
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1 non-stop flight per dayat least 3h 55minfrom $290 - Boston (BOS) Chicago Midway (MDW)
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2–6 non-stop flights per dayat least 2h 30minfrom $249 - Los Angeles (LAX) Chicago Midway (MDW)
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2–5 non-stop flights per dayat least 3hfrom $279 - Orlando (MCO) Chicago Midway (MDW)
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1–9 non-stop flights per dayat least 2h 40minfrom $200 - Atlanta (ATL) Chicago Midway (MDW)
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up to 5 non-stop flights per dayat least 1h 45minfrom $131 - Tampa (TPA) Chicago Midway (MDW)
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up to 6 non-stop flights per dayat least 2h 35minfrom $243 - Minneapolis (MSP) Chicago Midway (MDW)
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2–6 non-stop flights per dayat least 1h 25minfrom $213