$84+ Cheap flights from Midway (MDW) to New Hampshire
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MHT
Jun 1 — Jun 81
Round-trip
1 adult, Economy
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Find cheap flights from Midway to New Hampshire with Cheapflights
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Cheapest flights from Midway to New HampshireExplore the most affordable flight options available from Midway to New Hampshire. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 2, 2026.
Explore the most affordable flight options available from Midway to New Hampshire. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 2, 2026.
This Expedia deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2012:04 pm
MDW
- BOS
1 stop12h 20m
Frontier
Mon 6/112:01 pm
BOS
- MDW
1 stop11h 01m
Frontier
Deal found 4/28![Frontier logo]()
$160
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 6/165:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 4/27![Southwest logo]()
$167
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/205:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 6/245:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 4/28![Southwest logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/212:27 pm
MDW
- BOS
1 stop11h 57m
Frontier
Wed 6/36:00 am
BOS
- MDW
1 stop17h 02m
Frontier
Deal found 4/28![Frontier logo]()
$175
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 6/98:55 am
BOS
- MDW
1 stop6h 05m
Southwest
Deal found 4/27![Southwest logo]()
$177
This Frontier deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:27 pm
MDW
- BOS
1 stop11h 57m
Frontier
Mon 6/16:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Deal found 4/30![Frontier logo]()
$180
This Expedia deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1312:04 pm
MDW
- BOS
1 stop12h 20m
Frontier
Wed 5/2012:01 pm
BOS
- MDW
1 stop11h 01m
Frontier
Deal found 4/28![Frontier logo]()
$181
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1010:10 am
MDW
- BOS
2 stops6h 35m
Southwest
Wed 6/175:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 4/28![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 5/265:45 am
BOS
- MDW
1 stop10h 10m
Southwest
Deal found 4/27![Southwest logo]()
$183
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/127:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 6/175:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 4/28![Southwest logo]()
$186
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/57:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 6/85:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 4/28![Southwest logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:04 pm
MDW
- BOS
1 stop12h 20m
Frontier
Tue 6/99:10 am
BOS
- MDW
1 stop14h 01m
Frontier
Deal found 4/28![Frontier logo]()
$189
Best flights from Midway to New HampshireDiscover carefully curated flight deals from Midway to New Hampshire that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 2, 2026.
Discover carefully curated flight deals from Midway to New Hampshire that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 2, 2026.
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:40 am
MDW
- BOS
Nonstop2h 20m
Southwest
Mon 9/77:30 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/1![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/210:59 am
MDW
- PWM
2 stops11h 19m
Delta
Mon 6/86:00 am
PWM
- MDW
1 stop7h 00m
Delta
Deal found 4/27![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/57:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 6/83:55 pm
BOS
- MDW
1 stop7h 05m
Southwest
Deal found 4/29![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Wed 6/36:20 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 4/27![Southwest logo]()
$236
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:25 pm
MDW
- BOS
1 stop5h 15m
Southwest
Sat 5/307:15 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 5/1![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/21:22 pm
MDW
- PWM
2 stops8h 47m
Delta
Tue 6/96:00 am
PWM
- MDW
2 stops11h 16m
Delta
Deal found 4/27![Delta logo]()
$300
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/205:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 6/248:55 am
BOS
- MDW
2 stops7h 40m
Southwest
Deal found 4/30![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/231:22 pm
MDW
- PWM
2 stops8h 47m
Delta
Sun 5/2410:57 am
PWM
- MDW
2 stops11h 12m
Delta
Deal found 5/1![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/189:20 am
MDW
- BOS
Nonstop2h 20m
Southwest
Sun 6/2110:05 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 4/29![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/112:45 pm
MDW
- BOS
1 stop7h 40m
Southwest
Sat 6/205:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 4/28![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/67:45 am
MDW
- BOS
1 stop6h 15m
Southwest
Sun 9/138:00 am
BOS
- MDW
2 stops9h 35m
Southwest
Deal found 5/1![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/295:30 am
MDW
- BOS
1 stop8h 40m
Southwest
Sun 5/315:30 am
BOS
- MDW
2 stops8h 35m
Southwest
Deal found 5/1![Southwest logo]()
$278
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/171:00 pm
MDW
- BOS
2 stops7h 40m
Southwest
Wed 7/225:25 am
BOS
- MDW
1 stop4h 15m
Southwest
Deal found 4/27![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/117:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 6/1410:05 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 4/27![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/27:00 pm
MDW
- PWM
1 stop4h 05m
Southwest
Tue 7/75:30 am
PWM
- MDW
1 stop6h 30m
Southwest
Deal found 4/29![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:00 am
MDW
- PWM
1 stop4h 20m
Southwest
Mon 6/85:35 am
PWM
- MDW
1 stop6h 00m
Southwest
Deal found 4/27![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:50 am
MDW
- MHT
2 stops8h 30m
Southwest
Tue 6/93:55 pm
MHT
- MDW
1 stop4h 40m
Southwest
Deal found 4/29![Southwest logo]()
$334
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:45 am
MDW
- PWM
2 stops6h 15m
Southwest
Tue 9/297:45 am
PWM
- MDW
Nonstop2h 35m
Southwest
Deal found 4/30![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:50 pm
MDW
- PWM
Nonstop2h 15m
Southwest
Fri 8/77:40 am
PWM
- MDW
Nonstop2h 30m
Southwest
Deal found 4/26![Southwest logo]()
$340
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/125:00 pm
MDW
- MHT
1 stop4h 30m
Southwest
Sat 5/167:40 am
MHT
- MDW
Nonstop2h 30m
Southwest
Deal found 4/27![Southwest logo]()
$349
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:10 pm
MDW
- PWM
Nonstop2h 20m
Southwest
Sun 9/277:40 am
PWM
- MDW
Nonstop2h 30m
Southwest
Deal found 5/1![Southwest logo]()
$361
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:15 pm
MDW
- PWM
Nonstop2h 15m
Southwest
Sat 10/104:40 pm
PWM
- MDW
Nonstop2h 30m
Southwest
Deal found 4/29![Southwest logo]()
$368
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/75:30 pm
MDW
- MHT
1 stop4h 15m
Southwest
Thu 7/96:45 am
MHT
- MDW
Nonstop2h 25m
Southwest
Deal found 4/27![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:15 pm
MDW
- PWM
Nonstop2h 15m
Southwest
Thu 7/27:40 am
PWM
- MDW
Nonstop2h 35m
Southwest
Deal found 4/30![Southwest logo]()
$384
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/165:00 am
MDW
- PWM
1 stop6h 45m
Southwest
Thu 8/203:40 pm
PWM
- MDW
2 stops7h 40m
Southwest
Deal found 4/30![Southwest logo]()
$386
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:05 pm
MDW
- MHT
Nonstop2h 10m
Southwest
Fri 7/1011:30 am
MHT
- MDW
2 stops7h 25m
Southwest
Deal found 4/29![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/265:55 pm
MDW
- MHT
Nonstop2h 10m
Southwest
Fri 5/297:25 am
MHT
- MDW
Nonstop2h 30m
Southwest
Deal found 4/28![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/255:50 pm
MDW
- MHT
Nonstop2h 10m
Southwest
Sat 8/15:35 am
MHT
- MDW
2 stops9h 20m
Southwest
Deal found 4/30![Southwest logo]()
$397
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:45 pm
MDW
- MHT
Nonstop2h 10m
Southwest
Sun 6/147:10 pm
MHT
- MDW
Nonstop2h 30m
Southwest
Deal found 4/29![Southwest logo]()
$406
Last-minute flights from Midway to New HampshireDiscover last-minute flight deals from Midway to New Hampshire. Data last updated May 2, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to New Hampshire. Data last updated May 2, 2026 and is based on user searches.
This Travelocity deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/84:52 pm
MDW
- BOS
1 stop15h 20m
Frontier
Sat 5/2312:01 pm
BOS
- MDW
1 stop11h 01m
Frontier
Deal found 4/30![Frontier logo]()
$186
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/123:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 5/1910:45 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 4/28![Southwest logo]()
$177
This Expedia deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1312:04 pm
MDW
- BOS
1 stop12h 20m
Frontier
Wed 5/2012:01 pm
BOS
- MDW
1 stop11h 01m
Frontier
Deal found 4/28![Frontier logo]()
$181
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/191:55 pm
MDW
- BOS
1 stop7h 25m
Southwest
Tue 5/266:20 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 4/30![Southwest logo]()
$187
This Expedia deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2012:04 pm
MDW
- BOS
1 stop12h 20m
Frontier
Mon 6/112:01 pm
BOS
- MDW
1 stop11h 01m
Frontier
Deal found 4/28![Frontier logo]()
$160
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 5/267:20 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 4/28![Southwest logo]()
$167
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Mon 6/16:55 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 4/28![Southwest logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:30 pm
MDW
- BOS
1 stop11h 26m
Multiple Airlines
Tue 6/29:12 am
BOS
- MDW
1 stop13h 50m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$195
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/291:22 pm
MDW
- PWM
2 stops8h 47m
Delta
Mon 6/112:50 pm
PWM
- MDW
1 stop6h 43m
Delta
Deal found 4/28![Delta logo]()
$294
This Frontier deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3011:59 am
MDW
- BOS
1 stop12h 25m
Frontier
Mon 6/112:01 pm
BOS
- MDW
1 stop11h 01m
Frontier
Deal found 4/28![Frontier logo]()
$180
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 6/210:45 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 4/30![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 6/36:20 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 4/28![Southwest logo]()
$192
One-way flights from Midway to New HampshireSearch for one-way flight options from Midway to New Hampshire. Find affordable one-way fares based on user searches. Data last updated May 2, 2026.
Search for one-way flight options from Midway to New Hampshire. Find affordable one-way fares based on user searches. Data last updated May 2, 2026.
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/27![Southwest logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1012:04 pm
MDW
- BOS
1 stop12h 23m
Frontier
Deal found 4/27![Frontier logo]()
$86
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/75:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 4/29![Southwest logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:04 pm
MDW
- BOS
1 stop12h 20m
Frontier
Deal found 4/28![Frontier logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/212:27 pm
MDW
- BOS
1 stop11h 57m
Frontier
Deal found 4/27![Frontier logo]()
$93
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/105:30 pm
MDW
- BOS
1 stop4h 50m
Southwest
Deal found 4/27![Southwest logo]()
$94
This Super.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1512:04 pm
MDW
- BOS
1 stop12h 20m
Frontier
Deal found 4/29![Frontier logo]()
$95
This Travelocity deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:27 pm
MDW
- BOS
1 stop11h 57m
Frontier
Deal found 4/30![Frontier logo]()
$96
This Frontier deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/112:04 pm
MDW
- BOS
1 stop12h 20m
Frontier
Deal found 4/28![Frontier logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:30 pm
MDW
- BOS
1 stop11h 26m
Allegiant Air
Deal found 5/1![Allegiant Air logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1612:27 pm
MDW
- BOS
1 stop18h 25m
Frontier
Deal found 4/30![Frontier logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:04 pm
MDW
- PWM
2 stops30h 12m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$133
Find flight deals from Midway to New Hampshire
Keep the following information in mind while searching for Midway to New Hampshire flight deals. Data was last updated May 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $160 (Expedia) |
One-way from | $84 (Southwest) |
Popular in | April |
Cheapest in | January |
Average price | $222 |
Good one-way deal | $197 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to New Hampshire that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 2, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to New Hampshire that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 9/5
7:40 am-11:00 am
Nonstop2h 20m
Boston Logan Intl
Mon 9/7
7:30 am-9:05 am
Nonstop2h 35m
$207
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 6/5
7:35 pm-10:50 pm
Nonstop2h 15m
Boston Logan Intl
Mon 6/8
3:55 pm-10:00 pm
1 stop7h 05m
$217
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Wed 5/27
6:00 pm-9:20 pm
Nonstop2h 20m
Boston Logan Intl
Wed 6/3
6:20 pm-8:10 pm
Nonstop2h 50m
$236
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 5/23
5:25 pm-11:40 pm
1 stop5h 15m
Boston Logan Intl
Sat 5/30
7:15 am-9:05 am
Nonstop2h 50m
$247
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 6/20
5:25 am-8:40 am
Nonstop2h 15m
Boston Logan Intl
Wed 6/24
8:55 am-3:35 pm
2 stops7h 40m
$257
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Thu 6/18
9:20 am-12:40 pm
Nonstop2h 20m
Boston Logan Intl
Sun 6/21
10:05 pm-11:45 pm
Nonstop2h 40m
$262
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Thu 6/11
2:45 pm-11:25 pm
1 stop7h 40m
Boston Logan Intl
Sat 6/20
5:20 am-6:55 am
Nonstop2h 35m
$267
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sun 9/6
7:45 am-3:00 pm
1 stop6h 15m
Boston Logan Intl
Sun 9/13
8:00 am-4:35 pm
2 stops9h 35m
$277
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 5/29
5:30 am-3:10 pm
1 stop8h 40m
Boston Logan Intl
Sun 5/31
5:30 am-1:05 pm
2 stops8h 35m
$278
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 7/17
1:00 pm-9:40 pm
2 stops7h 40m
Boston Logan Intl
Wed 7/22
5:25 am-8:40 am
1 stop4h 15m
$286
Showing 1-10 of 55 resultsSorted by cheapest first
Best time to book a flight from Midway to New Hampshire
Have a flexible travel schedule? Discover the best time to fly to New Hampshire from Midway with our price prediction graph.
MDW-BOS
MDW-PWM
MDW-MHT
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to New Hampshire
MDW-USNH
MDW-BOS
MDW-PWM
MDW-MHT
What is the cheapest time of day to fly from MDW to NH?
Find hourly flight availability from Midway to New Hampshire. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 2, 2026.
One of the essential ways to save on airfare from Chicago Midway Airport to New Hampshire is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 21% on airfare.
What is the cheapest day to fly from Chicago Midway Airport to New Hampshire?
Use this chart to determine the cheapest time to fly round-trip from Midway to New Hampshire. Price data was last updated on April 25, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to New Hampshire flight should consider departing on Saturday mornings when fares are most often at their lowest. Friday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing New Hampshire
Get insights into the airlines that provide service to New Hampshire. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to New Hampshire. Reviews last updated May 2, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to New Hampshire, such as Southwest. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Midway to New Hampshire. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Midway to New Hampshire
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Complete your trip
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Find flights from Midway to New Hampshire, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and New Hampshire flights
Browse other Midway and New Hampshire flight options. Last updated on May 2, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Midway to New Hampshire flights
Consider these flights traveling from Midway to New Hampshire.
Top airline flying from Midway to New Hampshire
Discover the top airline that operate flights from Midway to New Hampshire. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$181 | Average$423 | FlexibilityNo cancel fee | On-time63% |