Direct flights from O'Hare / Midway. From $220-400 round trip. Flight time: ~4h 30m.
$220
Starting at
4h 30m
Flight time
September
Cheapest month
Yes
Direct flights
O'Hare has more direct flights but Midway (Spirit/Frontier) is often cheaper
Chicago winter escape deals to DR appear in October — set fare alerts early
Consider connecting through Miami or Fort Lauderdale for savings of $50-100
New York
From $180
Miami
From $120
Boston
From $200
Atlanta
From $200
Houston
From $220
Los Angeles
From $300
Philadelphia
From $190
Washington D.C.
From $200
Orlando
From $150
Dallas
From $230
Charlotte
From $200
San Francisco
From $320
Denver
From $280
Detroit
From $220
Minneapolis
From $230
Newark
From $170
Fort Lauderdale
From $100
Tampa
From $160
Seattle
From $350
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