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Find the best flight from Chicago to Winter Haven

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Low fares for Chicago (CHI) to Orlando (ORL)
Wed 05/30 - Tue 06/19
20 days
$190
Wed 06/13 - Wed 06/20
7 days, 1 stop max
$156
Wed 07/18 - Tue 07/24
6 days, 0 stops max
$162
Wed 08/29 - Wed 09/05
7 days, 0 stops max
$152
Mon 09/10 - Fri 09/14
4 days, 0 stops max
$158
Mon 10/01 - Tue 10/09
8 days, 0 stops max
$157
Tue 06/12 - Wed 06/13
1 day
$183
Wed 06/06 - Sun 06/17
11 days
$189
Fri 06/08 - Wed 06/20
12 days
$190
Tue 05/29 - Tue 06/05
7 days
$195
Wed 05/30 - Tue 06/05
6 days
$195
Thu 06/07 - Wed 06/20
13 days
$197
Thu 06/21 - Thu 07/05
14 days
$198
Sun 06/24 - Tue 06/26
2 days, 0 stops max
$202
Mon 07/02 - Tue 07/17
15 days
$202
Wed 06/27 - Sun 07/01
4 days, 0 stops max
$203
Tue 06/26 - Tue 07/10
14 days
$206
Mon 06/25 - Thu 07/05
10 days
$206
Hampton Inn Winter Haven
Hampton Inn Winter Haven
668 Reviews
Winter Haven, FL
from
Holiday Inn Winter Haven
Holiday Inn Winter Haven
254 Reviews
Winter Haven, FL
from
Best Western Auburndale Inn & Suites
Best Western Auburndale Inn & Suites
470 Reviews
Auburndale, FL
from
Holiday Inn Express Lake Wales N - Winter Haven
Holiday Inn Express Lake Wales N - Winter Haven
252 Reviews
Lake Wales, FL
from
Route information
  • Chicago, IL is 1,000 miles from Winter Haven
  • There are 63 weekly flights from Chicago, IL to Winter Haven
  • 37 non-stop flights are operating from Chicago, IL to Winter Haven today
  • Southwest Airlines has the most nonstop flights between Chicago, IL and Winter Haven
  • Atlanta, GA - Hartsfield-Jackson Atlanta Intl Airport is the most popular connection for one stop flights between Chicago, IL and Winter Haven
In-Flight Information
  • The average flying time for a direct flight from Chicago, IL to Winter Haven is 2 hours 40 minutes
  • Most direct flights leave around 8:15 CDT
  • Southwest Airlines flight #1944 is today's earliest flight from Chicago, IL to Winter Haven (6:00 CDT, Boeing 737-700 (winglets) pax)
  • Southwest Airlines flight #1310 is today's latest flight from Chicago, IL to Winter Haven (21:05 CDT, Boeing 737-700 (winglets) pax)
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Arrival information
  • Winter Haven is 37 mi from Orlando Intl Airport (Orlando, FL).
  • Orlando Intl Airport (Orlando, FL)
    • Right now, 73 airlines operate out of Orlando Intl Airport.
    • Orlando Intl Airport offers nonstop flights to 106 cities.
    • Every week, at least 2,983 domestic flights and 497 international flights depart from Orlando Intl Airport.
  • Winter Haven is 60 mi from Orlando Sanford International Airport (Orlando, FL).
  • Orlando Sanford International Airport (Orlando, FL)
    • Right now, 5 airlines operate out of Orlando Sanford International Airport.
    • Orlando Sanford International Airport offers nonstop flights to 77 cities.
    • Every week, at least 136 domestic flights and 11 international flights depart from Orlando Sanford International Airport.
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