Find the Cheapest Flight from Fort Myers (RSW) to Chicago (CHI)
Find the ideal departure and return dates from to Chicago and the cheapest flights of the month. We already found out the best options for you.
| Departure at | Return at | Airline | Find tickets |
|---|---|---|---|
| May 18, 2026 | May 23, 2026 | United Airlines | Tickets from 282 |
| May 19, 2026 | May 25, 2026 | United Airlines | Tickets from 273 |
| May 21, 2026 | May 25, 2026 | United Airlines | Tickets from 260 |
| June 19, 2026 | June 21, 2026 | Southwest Airlines | Tickets from 414 |
How Much is a Flight from Fort Myers?
What is the Best Airline to Fly from Fort Myers?
At cheapfly365 we give you all the available options from our reputable partners. We give you every one of the accessible choices from our legitimate accomplices. Select the aircraft that best suits your inclinations and participation loyalties.
| Airline | Destination | Find tickets |
|---|---|---|
| jetBlue | New York | Tickets from 207 |
| United Airlines | Chicago | Tickets from 260 |
| American Airlines | Boston | Tickets from 280 |
| Frontier Airlines | Denver | Tickets from 286 |
| Southwest Airlines | Nashville | Tickets from 300 |
| Sun Country Airlines | Minneapolis | Tickets from 205 |
| Avelo Airlines | Baltimore | Tickets from 260 |
| Southwest Airlines | Columbus | Tickets from 340 |
| Southwest Airlines | Philadelphia | Tickets from 387 |
| Southwest Airlines | Pittsburgh | Tickets from 417 |
| Air Canada | San Jose | Tickets from 630 |
| Southwest Airlines | Washington | Tickets from 300 |
| Discover Airlines | Almaty | Tickets from 1 908 |
| Frontier Airlines | Atlanta | Tickets from 216 |
| United Airlines | Budapest | Tickets from 1 027 |
| jetBlue | Buffalo | Tickets from 191 |
| Southwest Airlines | Belgrade | Tickets from 434 |
| United Airlines | Fort Lauderdale | Tickets from 736 |
| Southwest Airlines | Jacksonville | Tickets from 243 |
| Southwest Airlines | Los Angeles | Tickets from 295 |
| jetBlue | Saint Petersburg | Tickets from 2 427 |
| Frontier Airlines | Miami | Tickets from 339 |
| Southwest Airlines | Ontario | Tickets from 369 |
| Breeze Airways | Norfolk | Tickets from 485 |
| American Airlines | Portland | Tickets from 756 |
| United Airlines | Rome | Tickets from 1 240 |
| American Airlines | Rochester | Tickets from 561 |
| United Airlines | Saint Thomas | Tickets from 929 |
| Breeze Airways | Newburgh | Tickets from 261 |
| Breeze Airways | Zurich | Tickets from 1 157 |
Non-stop Flights from Fort Myers to Chicago – Leaving Soon
We have collected for you the flight ticket prices from to Chicago for the entire current month. Find the flight you're interested in with one-way. Don't forget to book a hotel and rental car before you travel.
| Departure at | Trip class | Distance | Find tickets |
|---|---|---|---|
| May 24, 2026 | Economy | 0 ml | Tickets from 198 |
| May 25, 2026 | Economy | 0 ml | Tickets from 198 |
| May 26, 2026 | Economy | 0 ml | Tickets from 198 |
| May 23, 2026 | Economy | 1122 ml | Tickets from 199 |
| June 30, 2026 | Economy | 1122 ml | Tickets from 145 |
Find Flights from Fort Myers to Chicago within your Budget
Easily find the cheapest day or month for your trip. You can choose direct or return flights but also you can choose one-way or the holiday duration system (choose from 1 to 30 days and you will be informed about the cheapest flights).
Fort Myers to Chicago Flight Deals
Are you looking to travel to Chicago in the coming months? The cheapest tickets we have for you.
| Departure at | Return at | Airline | Flight number | Find tickets |
|---|---|---|---|---|
| May 21, 2026 | May 25, 2026 | United Airlines | UA 2738 | Tickets from 260 |
| June 19, 2026 | June 21, 2026 | Southwest Airlines | WN 3470 | Tickets from 414 |
The Cheapest Return Flights from Fort Myers to Chicago
It is time to travel from to Chicago and you are looking for the cheapest round trip airfare. Well good for you! In the table below you can check the lowest prices from to Chicago.
| Departure at | Return at | Airline | Find tickets |
|---|---|---|---|
| May 21, 2026 | May 25, 2026 | United Airlines | Tickets from 260 |
Fly your Favorite Airline from Chicago
Looking for direct flight destinations from Chicago? We searched and found the best options for you.
| Origin - Destination | Departure at | Return at | Airline | Find tickets |
|---|---|---|---|---|
ChicagoAllentown | June 1, 2026 | June 7, 2026 | United Airlines | Tickets from 939 |
ChicagoAlbuquerque | June 18, 2026 | June 23, 2026 | United Airlines | Tickets from 385 |
ChicagoAmsterdam | July 1, 2026 | July 31, 2026 | KLM | Tickets from 1 094 |
ChicagoAnchorage | August 4, 2026 | August 11, 2026 | JetHunter | Tickets from 370 |
ChicagoAthens | July 9, 2026 | July 23, 2026 | United Airlines | Tickets from 1 091 |
Cheap Flights to Chicago Airport
Book the next cheap ticket to Chicago immediately. The table below shows from which cities you can find a cheap flight to Chicago airport.
| Origin - Destination | Departure at | Return at | Find tickets |
|---|---|---|---|
AtlantaChicago | July 3, 2026 | July 6, 2026 | Tickets from 106 |
DallasChicago | August 8, 2026 | August 14, 2026 | Tickets from 121 |
OrlandoChicago | July 18, 2026 | July 26, 2026 | Tickets from 123 |
MinneapolisChicago | June 17, 2026 | August 5, 2026 | Tickets from 126 |
PhoenixChicago | July 1, 2026 | July 7, 2026 | Tickets from 137 |
Direct Flights from Fort Myers
Find cheap flights from to top destinations. Start your next trip now!
| Origin - Destination | Departure at | Return at | Find tickets |
|---|---|---|---|
Fort MyersBuffalo | June 4, 2026 | June 7, 2026 | Tickets from 191 |
Fort MyersMinneapolis | June 19, 2026 | June 21, 2026 | Tickets from 205 |
Fort MyersNew York | June 1, 2026 | June 5, 2026 | Tickets from 207 |
Fort MyersAtlanta | May 28, 2026 | May 31, 2026 | Tickets from 217 |
Fort MyersJacksonville | May 22, 2026 | May 26, 2026 | Tickets from 243 |
Useful Information Before the Fort Myers – Chicago Flight
Found more than 66 flights every day. The average flight duration is 2h 55m. Below is the flight schedule with departures and arrivals of the day. The airline, the airports of the flight and the schedule of the week are also displayed.
Fort Myers, United StatesChicago, United States
| Time and stops | Airline | Route | Schedule | Find tickets |
|---|---|---|---|---|
05:3509:20 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
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06:0007:55 Direct | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
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06:1508:34 Direct | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
06:1510:47 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
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06:4511:04 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
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06:4511:56 1 Stop | Delta | RSW — MDW | S M T W T F S | Pick Dates |
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06:5008:45 Direct | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
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07:0008:55 Direct | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
07:0009:23 Direct | United Airlines | RSW — ORD | S M T W T F S | Pick Dates |
07:0009:23 Direct | United Airlines | RSW — ORD | S M T W T F S | Pick Dates |
07:0012:07 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
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07:0014:15 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
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07:0309:23 Direct | United Airlines | RSW — ORD | S M T W T F S | Pick Dates |
07:0309:23 Direct | United Airlines | RSW — ORD | S M T W T F S | Pick Dates |
07:2012:00 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
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07:5009:45 Direct | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
08:0011:56 1 Stop | Delta | RSW — MDW | S M T W T F S | Pick Dates |
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08:0612:36 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
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08:0614:20 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
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08:2510:43 Direct | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
08:2510:45 Direct | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
08:2511:40 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
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08:3712:36 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
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09:2015:45 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
09:2019:35 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
09:3014:55 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
09:5814:20 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
09:5815:59 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
09:5816:04 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
10:0012:10 Direct | Southwest Airlines | RSW — ORD | S M T W T F S | Pick Dates |
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10:0015:59 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
10:1512:10 Direct | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
10:2614:20 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
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10:5214:41 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
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11:3413:53 Direct | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
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12:3014:50 Direct | United Airlines | RSW — ORD | S M T W T F S | Pick Dates |
12:3014:53 Direct | United Airlines | RSW — ORD | S M T W T F S | Pick Dates |
12:4018:05 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
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13:0518:33 1 Stop | United Airlines | RSW — ORD | S M T W T F S | Pick Dates |
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13:1518:45 1 Stop | United Airlines | RSW — ORD | S M T W T F S | Pick Dates |
13:2118:35 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
13:2118:35 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
13:2118:41 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
13:2118:41 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
13:2119:07 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
13:2318:53 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
13:2818:41 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
13:3118:35 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
13:3119:07 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
13:3517:50 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
13:3519:35 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
13:3917:58 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
13:3918:53 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
13:3919:22 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
13:5017:58 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
13:5018:53 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
13:5019:22 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
14:0418:53 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
14:0419:32 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
14:0419:32 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
14:0419:32 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
14:0420:40 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
14:2919:27 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
14:2921:21 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
14:3016:53 Direct | United Airlines | RSW — ORD | S M T W T F S | Pick Dates |
14:3016:53 Direct | United Airlines | RSW — ORD | S M T W T F S | Pick Dates |
14:3120:33 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
14:3120:33 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
14:3120:33 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
14:3120:33 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
14:3121:19 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
14:3121:39 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
14:3121:39 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
14:4019:30 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
14:5516:55 Direct | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
14:5821:21 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
14:5821:42 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
14:5821:42 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
14:5920:22 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
14:5920:22 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
14:5921:35 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
15:0017:15 Direct | Southwest Airlines | RSW — ORD | S M T W T F S | Pick Dates |
15:0219:22 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
15:0520:22 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
15:0521:35 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
15:1517:30 Direct | Southwest Airlines | RSW — ORD | S M T W T F S | Pick Dates |
15:4120:24 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:4120:26 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:4120:26 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:4120:28 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:4120:32 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:4120:32 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:4121:09 1 Stop | Delta | RSW — MDW | S M T W T F S | Pick Dates |
15:4121:09 1 Stop | Delta | RSW — MDW | S M T W T F S | Pick Dates |
15:4121:09 1 Stop | Delta | RSW — MDW | S M T W T F S | Pick Dates |
15:4121:21 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:4121:21 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:4121:34 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:4520:15 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
15:4520:26 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:4520:26 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:4520:26 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:4520:28 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:4520:28 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:4520:32 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:4520:32 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:4521:09 1 Stop | Delta | RSW — MDW | S M T W T F S | Pick Dates |
15:4521:09 1 Stop | Delta | RSW — MDW | S M T W T F S | Pick Dates |
15:4521:09 1 Stop | Delta | RSW — MDW | S M T W T F S | Pick Dates |
15:4521:21 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:4521:21 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:4521:34 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:4521:34 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:4521:53 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:4521:53 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:5721:37 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
15:5721:39 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
16:0019:40 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
16:1521:50 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
16:1521:50 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
16:2520:05 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
16:3518:35 Direct | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
16:3618:57 Direct | United Airlines | RSW — ORD | S M T W T F S | Pick Dates |
16:3718:56 Direct | United Airlines | RSW — ORD | S M T W T F S | Pick Dates |
16:3919:00 Direct | United Airlines | RSW — ORD | S M T W T F S | Pick Dates |
16:4219:05 Direct | United Airlines | RSW — ORD | S M T W T F S | Pick Dates |
16:5022:20 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
17:2619:55 Direct | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
17:3519:30 Direct | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
17:3523:38 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
17:3720:06 Direct | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
17:4021:25 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
17:4521:25 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
17:4521:55 1 Stop | Southwest Airlines | RSW — ORD | S M T W T F S | Pick Dates |
17:4621:46 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
17:4621:49 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
17:4622:27 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
17:5022:40 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
17:5521:55 1 Stop | Southwest Airlines | RSW — ORD | S M T W T F S | Pick Dates |
17:5522:35 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
17:5921:53 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
17:5921:53 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
17:5921:53 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
17:5921:53 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
17:5921:53 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
17:5921:53 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
17:5923:59 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
17:5923:59 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
17:5923:59 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
17:5923:59 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
18:0021:55 1 Stop | Southwest Airlines | RSW — ORD | S M T W T F S | Pick Dates |
18:1521:50 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
18:1521:50 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
18:3022:35 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
18:3321:00 Direct | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
18:4022:15 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
18:4022:15 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
18:5023:54 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
19:1022:45 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
19:1022:45 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
19:1022:55 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
19:4123:54 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
19:5023:30 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
19:5023:59 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
19:5023:59 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
19:5023:59 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
20:2522:20 Direct | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
