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prices we've seen · United States fares · USD

Flights from New York (LGA) to Chicago (MDW)

  • One way from $101
  • Round trip from $161
  • Nonstop on 29 of 31 dates
  • Fastest 2h 20m
  • 2 airlines

The cheapest one-way fare from New York to Chicago we have seen is $101 USD, departing Dec 31 (seen Oct 23): Southwest Airlines WN 2579, nonstop, 2h 40m.

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Prices are the fare alone; the seller shows the bag and fare rules.

Cheapest by month

Checked Oct 26

Pick a month to search the day its cheapest fare leaves.

  1. Oct 2026$172
  2. Nov 2026$101
  3. Dec 2026$101
  4. Jan 2027$103
  5. Feb 2027$130
  6. Mar 2027$115
  7. Apr 2027$178
  8. May 2027$191

Cheapest days to fly one wayCheapest round trips

Each day's cheapest fare we've seen, nonstop and with stops. Cheapest first.

We may earn a commission from the seller · How we rank

  1. ThuDec 31

    18:35

    2h 40mNonstop

    20:15

    Cheapest$101 USD

    Southwest Airlines WN 2579 · seen Oct 23

    Go to seller — $101

  2. TueNov 17

    09:29

    9h 18m1 stop

    17:47

    $101 USD

    Frontier F9 4347 · seen Oct 25

    Go to seller — $101

  3. WedNov 18

    09:29

    9h 18m1 stop

    17:47

    $102 USD

    Frontier F9 4347 · seen Oct 25

    Go to seller — $102

  4. ThuDec 10

    06:40

    2h 25mNonstop

    08:05

    $105 USD

    Southwest Airlines WN 982 · seen Oct 22

    Go to seller — $105

  5. ThuNov 12

    08:30

    2h 35mNonstop

    10:05

    $105 USD

    Southwest Airlines WN 1138 · seen Oct 23

    Go to seller — $105

  6. MonDec 7

    06:30

    11h 46m1 stop

    17:16

    $105 USD

    Frontier F9 2431 · seen Oct 20

    Go to seller — $105

  7. SunNov 22

    06:45

    2h 25mNonstop

    08:10

    $106 USD

    Southwest Airlines WN 982 · seen Oct 23

    Go to seller — $106

  8. FriDec 25

    18:35

    2h 40mNonstop

    20:15

    $107 USD

    Southwest Airlines WN 2579 · seen Oct 23

    Go to seller — $107

  9. MonDec 7

    17:35

    2h 40mNonstop

    19:15

    $114 USD

    Southwest Airlines WN 1257 · seen Oct 20

    Go to seller — $114

  10. ThuNov 19

    17:30

    7h 17m1 stop

    23:47

    $115 USD

    Frontier F9 3453 · seen Oct 25

    Go to seller — $115
Show 39 more fares

  1. TueNov 10

    17:30

    7h 17m1 stop

    23:47

    $117 USD

    Frontier F9 3453 · seen Oct 26

    Go to seller — $117

  2. SatNov 21

    06:41

    8h 4m1 stop

    13:45

    $117 USD

    Frontier F9 3457 · seen Oct 25

    Go to seller — $117

  3. WedNov 4

    17:30

    7h 17m1 stop

    23:47

    $132 USD

    Frontier F9 3453 · seen Oct 25

    Go to seller — $132

  4. MonNov 16

    06:30

    12h 17m1 stop

    17:47

    $136 USD

    Frontier F9 3287 · seen Oct 23

    Go to seller — $136

  5. MonNov 23

    06:30

    6h 51m1 stop

    12:21

    $143 USD

    Frontier F9 3457 · seen Oct 25

    Go to seller — $143

  6. WedNov 18

    08:30

    2h 35mNonstop

    10:05

    $144 USD

    Southwest Airlines WN 120 · seen Oct 25

    Go to seller — $144

  7. TueNov 17

    12:30

    2h 35mNonstop

    14:05

    $147 USD

    Southwest Airlines WN 2576 · seen Oct 25

    Go to seller — $147

  8. FriNov 20

    06:30

    6h 25m1 stop

    11:55

    $147 USD

    Frontier F9 3457 · seen Oct 25

    Go to seller — $147

  9. WedDec 9

    17:30

    27h 12m2 stops

    19:42+1

    $147 USD

    Frontier F9 3457 · seen Oct 25

    Go to seller — $147

  10. WedDec 9

    15:15

    2h 45mNonstop

    17:00

    $148 USD

    Southwest Airlines WN 766 · seen Oct 25

    Go to seller — $148

  11. ThuNov 19

    12:30

    2h 35mNonstop

    14:05

    $152 USD

    Southwest Airlines WN 2576 · seen Oct 25

    Go to seller — $152

  12. SatNov 21

    19:55

    2h 30mNonstop

    21:25

    $156 USD

    Southwest Airlines WN 2578 · seen Oct 25

    Go to seller — $156

  13. MonNov 9

    06:30

    12h 17m1 stop

    17:47

    $159 USD

    Frontier F9 3287 · seen Oct 25

    Go to seller — $159

  14. FriDec 11

    06:30

    11h 46m1 stop

    17:16

    $160 USD

    Frontier F9 2431 · seen Oct 25

    Go to seller — $160

  15. FriDec 11

    06:45

    2h 25mNonstop

    08:10

    $162 USD

    Southwest Airlines WN 982 · seen Oct 25

    Go to seller — $162

  16. MonNov 23

    06:45

    2h 25mNonstop

    08:10

    $164 USD

    Southwest Airlines WN 982 · seen Oct 25

    Go to seller — $164

  17. SunNov 15

    07:15

    7h 55m1 stop

    14:10

    $166 USD

    Southwest Airlines WN 2651 · seen Oct 22

    Go to seller — $166

  18. TueNov 10

    12:30

    2h 35mNonstop

    14:05

    $169 USD

    Southwest Airlines WN 2576 · seen Oct 26

    Go to seller — $169

  19. FriNov 20

    10:20

    2h 50mNonstop

    12:10

    $171 USD

    Southwest Airlines WN 834 · seen Oct 25

    Go to seller — $171

  20. TueOct 27

    17:30

    7h 17m1 stop

    23:47

    $172 USD

    Frontier F9 3453 · seen Oct 26

    Go to seller — $172

  21. WedOct 28

    17:30

    7h 17m1 stop

    23:47

    $172 USD

    Frontier F9 3453 · seen Oct 26

    Go to seller — $172

  22. ThuNov 5

    06:30

    12h 17m1 stop

    17:47

    $177 USD

    Frontier F9 3287 · seen Oct 26

    Go to seller — $177

  23. MonNov 16

    08:30

    2h 35mNonstop

    10:05

    $178 USD

    Southwest Airlines WN 120 · seen Oct 23

    Go to seller — $178

  24. MonNov 9

    20:55

    2h 35mNonstop

    22:30

    $179 USD

    Southwest Airlines WN 2579 · seen Oct 25

    Go to seller — $179

  25. WedDec 30

    06:30

    9h 25m1 stop

    14:55

    $179 USD

    Southwest Airlines WN 4645 · seen Oct 22

    Go to seller — $179

  26. ThuOct 29

    12:30

    2h 20mNonstop

    13:50

    $193 USD

    Southwest Airlines WN 4333 · seen Oct 26

    Go to seller — $193

  27. WedDec 30

    08:30

    2h 35mNonstop

    10:05

    $198 USD

    Southwest Airlines WN 1138 · seen Oct 22

    Go to seller — $198

  28. ThuDec 24

    18:35

    2h 40mNonstop

    20:15

    $206 USD

    Southwest Airlines WN 2579 · seen Oct 23

    Go to seller — $206

  29. SunNov 15

    06:45

    2h 25mNonstop

    08:10

    $210 USD

    Southwest Airlines WN 982 · seen Oct 22

    Go to seller — $210

  30. MonNov 30

    20:50

    11h 35m1 stop

    07:25+1

    $221 USD

    Southwest Airlines WN 2572 · seen Oct 20

    Go to seller — $221

  31. WedNov 4

    17:35

    2h 40mNonstop

    19:15

    $238 USD

    Southwest Airlines WN 1257 · seen Oct 25

    Go to seller — $238

  32. ThuNov 5

    10:20

    2h 50mNonstop

    12:10

    $238 USD

    Southwest Airlines WN 834 · seen Oct 26

    Go to seller — $238

  33. MonNov 30

    12:00

    2h 50mNonstop

    13:50

    $246 USD

    Southwest Airlines WN 2576 · seen Oct 20

    Go to seller — $246

  34. ThuNov 26

    08:30

    2h 35mNonstop

    10:05

    $247 USD

    Southwest Airlines WN 1138 · seen Oct 23

    Go to seller — $247

  35. TueNov 24

    06:30

    2h 25mNonstop

    07:55

    $251 USD

    Southwest Airlines WN 2573 · seen Oct 23

    Go to seller — $251

  36. MonDec 21

    06:30

    14h1 stop

    19:30

    $301 USD

    Frontier F9 2431 · seen Oct 21

    Go to seller — $301

  37. WedNov 25

    17:05

    2h 35mNonstop

    18:40

    $306 USD

    Southwest Airlines WN 2578 · seen Oct 25

    Go to seller — $306

  38. MonDec 21

    08:30

    2h 35mNonstop

    10:05

    $328 USD

    Southwest Airlines WN 1138 · seen Oct 21

    Go to seller — $328

  39. WedDec 23

    17:05

    2h 35mNonstop

    18:40

    $376 USD

    Southwest Airlines WN 2578 · seen Oct 24

    Go to seller — $376

The cheapest round trips we've seen on this route, on any dates, cheapest first.

We may earn a commission from the seller · How we rank

  1. 7 nightsNov 11–18

    09:29

    MDW

    Cheapest$161 USD

    Frontier F9 4347 · 2 stops · 18h 11m in all, both ways · seen Oct 22

    Go to seller — $161

  2. 7 nightsNov 11–18

    18:35

    20:15

    $162 USD

    Southwest Airlines WN 2579 · Nonstop · 4h 45m in all, both ways · seen Oct 22

    Go to seller — $162

  3. 7 nightsNov 19–26

    15:15

    17:00

    $192 USD

    Southwest Airlines WN 766 · Nonstop · 4h 50m in all, both ways · seen Oct 21

    Go to seller — $192

  4. 4 nightsNov 11–15

    12:30

    14:05

    $193 USD

    Southwest Airlines WN 2576 · Nonstop · 4h 40m in all, both ways · seen Oct 23

    Go to seller — $193

  5. 7 nightsDec 9–16

    08:30

    10:05

    $194 USD

    Southwest Airlines WN 120 · Nonstop · 4h 40m in all, both ways · seen Oct 20

    Go to seller — $194

  6. 3 nightsNov 13–16

    15:05

    16:45

    $194 USD

    Southwest Airlines WN 432 · Nonstop · 4h 45m in all, both ways · seen Oct 24

    Go to seller — $194

  7. 9 nightsNov 23 – Dec 2

    10:20

    12:10

    $194 USD

    Southwest Airlines WN 834 · Nonstop · 4h 55m in all, both ways · seen Oct 23

    Go to seller — $194

  8. 4 nightsJan 1–5

    08:30

    10:05

    $196 USD

    Southwest Airlines WN 120 · Nonstop · 4h 40m in all, both ways · seen Oct 21

    Go to seller — $196

  9. 3 nightsJan 17–20

    20:55

    22:35

    $203 USD

    Southwest Airlines WN 2327 · Nonstop · 4h 45m in all, both ways · seen Oct 23

    Go to seller — $203

  10. 1 nightNov 11–12

    17:30

    MDW

    $226 USD

    Frontier F9 3453 · 2 stops · 15h 12m in all, both ways · seen Oct 21

    Go to seller — $226
Show 47 more fares

  1. 4 nightsDec 10–14

    09:15

    MDW

    $241 USD

    Frontier F9 3287 · 2 stops · 33h 38m in all, both ways · seen Oct 26

    Go to seller — $241

  2. 4 nightsDec 10–14

    18:35

    20:15

    $243 USD

    Southwest Airlines WN 2579 · Nonstop · 4h 50m in all, both ways · seen Oct 26

    Go to seller — $243

  3. 17 nightsDec 2–19

    17:05

    MDW

    $245 USD

    Southwest Airlines WN 2583 · 1 stop · 7h 35m in all, both ways · seen Oct 25

    Go to seller — $245

  4. 17 nightsDec 2–19

    08:30

    10:05

    $254 USD

    Southwest Airlines WN 120 · Nonstop · 4h 40m in all, both ways · seen Oct 25

    Go to seller — $254

  5. 2 nightsNov 7–9

    17:30

    MDW

    $257 USD

    Frontier F9 3453 · 2 stops · 17h 42m in all, both ways · seen Oct 23

    Go to seller — $257

  6. 28 nightsOct 29 – Nov 26

    20:55

    22:20

    $259 USD

    Southwest Airlines WN 494 · Nonstop · 4h 30m in all, both ways · seen Oct 25

    Go to seller — $259

  7. 1 nightNov 11–12

    06:40

    08:05

    $268 USD

    Southwest Airlines WN 982 · Nonstop · 4h 30m in all, both ways · seen Oct 21

    Go to seller — $268

  8. 2 nightsNov 8–10

    17:30

    MDW

    $272 USD

    Frontier F9 3453 · 2 stops · 16h 10m in all, both ways · seen Oct 22

    Go to seller — $272

  9. 2 nightsNov 20–22

    08:30

    10:05

    $273 USD

    Southwest Airlines WN 1138 · Nonstop · 4h 40m in all, both ways · seen Oct 21

    Go to seller — $273

  10. 3 nightsNov 21–24

    06:41

    MDW

    $273 USD

    Frontier F9 3457 · 2 stops · 13h 48m in all, both ways · seen Oct 25

    Go to seller — $273

  11. 4 nightsDec 9–13

    18:35

    20:15

    $274 USD

    Southwest Airlines WN 2579 · Nonstop · 4h 45m in all, both ways · seen Oct 26

    Go to seller — $274

  12. 1 nightNov 21–22

    19:55

    21:25

    $279 USD

    Southwest Airlines WN 2578 · Nonstop · 4h 35m in all, both ways · seen Oct 19

    Go to seller — $279

  13. 5 nightsNov 11–16

    17:30

    MDW

    $294 USD

    Frontier F9 3453 · 2 stops · 19h 44m in all, both ways · seen Oct 25

    Go to seller — $294

  14. 2 nightsNov 8–10

    06:45

    08:10

    $295 USD

    Southwest Airlines WN 982 · Nonstop · 4h 30m in all, both ways · seen Oct 22

    Go to seller — $295

  15. 3 nightsNov 19–22

    10:00

    11:40

    $298 USD

    Southwest Airlines WN 834 · Nonstop · 4h 45m in all, both ways · seen Oct 25

    Go to seller — $298

  16. 4 nightsDec 14–18

    18:45

    20:25

    $322 USD

    Southwest Airlines WN 2579 · Nonstop · 4h 45m in all, both ways · seen Oct 20

    Go to seller — $322

  17. 5 nightsDec 25–30

    18:35

    20:15

    $323 USD

    Southwest Airlines WN 2579 · Nonstop · 4h 45m in all, both ways · seen Oct 24

    Go to seller — $323

  18. 7 nightsDec 18–25

    10:05

    11:45

    $328 USD

    Southwest Airlines WN 834 · Nonstop · 4h 45m in all, both ways · seen Oct 19

    Go to seller — $328

  19. 4 nightsOct 28 – Nov 1

    17:30

    MDW

    $334 USD

    Frontier F9 3453 · 2 stops · 14h 56m in all, both ways · seen Oct 25

    Go to seller — $334

  20. 3 nightsNov 12–15

    17:30

    MDW

    $347 USD

    Frontier F9 3453 · 2 stops · 16h 10m in all, both ways · seen Oct 25

    Go to seller — $347

  21. 5 nightsNov 11–16

    12:30

    14:05

    $350 USD

    Southwest Airlines WN 2576 · Nonstop · 4h 40m in all, both ways · seen Oct 25

    Go to seller — $350

  22. 3 nightsNov 12–15

    10:20

    12:10

    $352 USD

    Southwest Airlines WN 834 · Nonstop · 4h 55m in all, both ways · seen Oct 25

    Go to seller — $352

  23. 2 nightsNov 7–9

    10:20

    12:10

    $353 USD

    Southwest Airlines WN 725 · Nonstop · 4h 55m in all, both ways · seen Oct 23

    Go to seller — $353

  24. 2 nightsOct 29–31

    06:30

    MDW

    $360 USD

    Frontier F9 3287 · 2 stops · 24h 38m in all, both ways · seen Oct 25

    Go to seller — $360

  25. 3 nightsOct 31 – Nov 3

    13:45

    15:05

    $368 USD

    Southwest Airlines WN 1667 · 1 stop · 9h 52m in all, both ways · seen Oct 25

    Go to seller — $368

  26. 3 nightsNov 21–24

    19:55

    21:25

    $371 USD

    Southwest Airlines WN 2578 · Nonstop · 4h 35m in all, both ways · seen Oct 25

    Go to seller — $371

  27. 4 nightsFeb 19–23

    08:30

    10:10

    $380 USD

    Southwest Airlines WN 2322 · Nonstop · 4h 45m in all, both ways · seen Oct 22

    Go to seller — $380

  28. 3 nightsOct 30 – Nov 2

    17:30

    MDW

    $383 USD

    Frontier F9 3453 · 2 stops · 14h 56m in all, both ways · seen Oct 26

    Go to seller — $383

  29. 3 nightsOct 29 – Nov 1

    06:30

    MDW

    $387 USD

    Frontier F9 3287 · 2 stops · 19h 56m in all, both ways · seen Oct 25

    Go to seller — $387

  30. 10 nightsDec 17–27

    06:45

    08:10

    $393 USD

    Southwest Airlines WN 0982 · Nonstop · 4h 30m in all, both ways · seen Oct 19

    Go to seller — $393

  31. 2 nightsMar 6–8

    07:00

    08:35

    $401 USD

    Southwest Airlines WN 2387 · Nonstop · 4h 40m in all, both ways · seen Oct 22

    Go to seller — $401

  32. 3 nightsMar 16–19

    08:30

    10:05

    $408 USD

    Southwest Airlines WN 2503 · Nonstop · 4h 35m in all, both ways · seen Oct 25

    Go to seller — $408

  33. 2 nightsOct 31 – Nov 2

    13:45

    15:05

    $409 USD

    Southwest Airlines WN 1667 · 1 stop · 9h 59m in all, both ways · seen Oct 25

    Go to seller — $409

  34. 2 nightsNov 25–27

    18:35

    20:15

    $432 USD

    Southwest Airlines WN 2579 · Nonstop · 4h 45m in all, both ways · seen Oct 22

    Go to seller — $432

  35. 2 nightsDec 22–24

    06:30

    07:55

    $433 USD

    Southwest Airlines WN 2573 · Nonstop · 4h 30m in all, both ways · seen Oct 23

    Go to seller — $433

  36. 2 nightsOct 29–31

    15:35

    16:55

    $438 USD

    Southwest Airlines WN 2544 · Nonstop · 4h 25m in all, both ways · seen Oct 25

    Go to seller — $438

  37. 3 nightsOct 27–30

    08:05

    09:25

    $438 USD

    Southwest Airlines WN 4430 · Nonstop · 4h 25m in all, both ways · seen Oct 25

    Go to seller — $438

  38. 4 nightsOct 28 – Nov 1

    08:05

    09:25

    $473 USD

    Southwest Airlines WN 4430 · Nonstop · 4h 20m in all, both ways · seen Oct 25

    Go to seller — $473

  39. 4 nightsDec 30 – Jan 3

    06:30

    MDW

    $474 USD

    Frontier F9 2431 · 2 stops · 39h 40m in all, both ways · seen Oct 22

    Go to seller — $474

  40. 7 nightsOct 26 – Nov 2

    20:55

    22:20

    $478 USD

    Southwest Airlines WN 494 · Nonstop · 4h 30m in all, both ways · seen Oct 25

    Go to seller — $478

  41. 3 nightsOct 30 – Nov 2

    15:35

    16:55

    $480 USD

    Southwest Airlines WN 2544 · Nonstop · 4h 20m in all, both ways · seen Oct 26

    Go to seller — $480

  42. 3 nightsOct 29 – Nov 1

    15:35

    16:55

    $482 USD

    Southwest Airlines WN 2544 · Nonstop · 4h 20m in all, both ways · seen Oct 25

    Go to seller — $482

  43. 2 nightsOct 31 – Nov 2

    10:05

    11:25

    $482 USD

    Southwest Airlines WN 1665 · Nonstop · 4h 25m in all, both ways · seen Oct 25

    Go to seller — $482

  44. 3 nightsOct 31 – Nov 3

    10:05

    11:25

    $482 USD

    Southwest Airlines WN 1665 · Nonstop · 4h 25m in all, both ways · seen Oct 25

    Go to seller — $482

  45. 5 nightsDec 29 – Jan 3

    06:30

    07:55

    $482 USD

    Southwest Airlines WN 2573 · Nonstop · 4h 30m in all, both ways · seen Oct 19

    Go to seller — $482

  46. 2 nightsNov 26–28

    08:30

    10:05

    $520 USD

    Southwest Airlines WN 1138 · Nonstop · 4h 40m in all, both ways · seen Oct 25

    Go to seller — $520

  47. 4 nightsDec 30 – Jan 3

    08:30

    10:05

    $527 USD

    Southwest Airlines WN 1138 · Nonstop · 4h 40m in all, both ways · seen Oct 22

    Go to seller — $527

Compare other routes

Compared with New York → Chicago: $101 one way (Dec 31).

Other places from New York

Every route from New York →

To Chicago from other cities

Every route to Chicago →

Airlines seen on this route

  • Frontier
  • Southwest Airlines

Marketing carriers; the operating airline is shown by the seller.

New York to Chicago in numbers

  • By month, Nov 2026 is the cheapest we've seen at $101 USD and May 2027 the most expensive at $191 USD — a spread of 89%.
  • Nonstop fares were seen on 29 of the 31 departure dates; carriers seen: Frontier, Southwest Airlines.
  • LGA serves New York, United States; MDW serves Chicago, United States.
  • Chicago runs 1 hour behind New York.

Questions

What is the cheapest fare from New York to Chicago?

The cheapest one-way fare from New York to Chicago we have seen is $101 USD, departing Dec 31 (seen Oct 23): Southwest Airlines WN 2579, nonstop, 2h 40m.

Is there a nonstop flight from New York to Chicago?

Nonstop fares were seen on 29 of the 31 departure dates; carriers seen: Frontier, Southwest Airlines.

Which month is cheapest to fly from New York to Chicago?

By month, Nov 2026 is the cheapest we've seen at $101 USD and May 2027 the most expensive at $191 USD — a spread of 89%.

How old is this price?

It is the cheapest fare we've seen for that date; the date beside it is the day it was seen, or our last check. We look again at least once a day for the routes people search, and stop showing a route's prices two days after our last look. The seller's page shows the price right now.

How does a2bflight rank results?

By price and duration only; commission never enters the order. Cheapest means cheapest among the fares we've seen for this route. A click that books may earn a2bflight a commission from the seller; the price you see is the seller's own. See how we rank and what we keep.