$216+ Cheap flights from Nassau (NAS) to Chicago (CHI)
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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
NAS — CHI
Jul 12 — Jul 191
Round-trip
1 adult, Economy
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Find cheap flights from Nassau to Chicago with Cheapflights
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Cheapest flights from Nassau to ChicagoExplore the most affordable flight options available from Nassau to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2026.
Explore the most affordable flight options available from Nassau to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2026.
This JetBlue deal was found by Cheapflights users on 6/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1512:20 pm
NAS
- ORD
1 stop12h 24m
JetBlue
Thu 7/167:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 6/10![JetBlue logo]()
$324
This JetBlue deal was found by Cheapflights users on 6/7. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:27 pm
NAS
- ORD
1 stop6h 17m
JetBlue
Sat 7/187:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 6/7![JetBlue logo]()
$325
This Justfly.com deal was found by Cheapflights users on 6/11. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:27 pm
NAS
- ORD
1 stop6h 17m
JetBlue
Wed 7/157:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 6/11![JetBlue logo]()
$334
This JetBlue deal was found by Cheapflights users on 6/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1512:20 pm
NAS
- ORD
1 stop12h 24m
JetBlue
Sun 7/197:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 6/10![JetBlue logo]()
$344
This JetBlue deal was found by Cheapflights users on 6/8. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1612:20 pm
NAS
- ORD
1 stop12h 24m
JetBlue
Tue 7/217:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 6/8![JetBlue logo]()
$353
This deal was found by Cheapflights users on 6/12. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:27 pm
NAS
- ORD
1 stop6h 17m
JetBlue
Wed 7/227:00 am
ORD
- NAS
1 stop5h 50m
JetBlue
Deal found 6/12![JetBlue logo]()
$371
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:11 pm
NAS
- ORD
1 stop7h 44m
American Airlines
Fri 9/47:30 am
ORD
- NAS
1 stop6h 03m
American Airlines
Deal found 6/10![American Airlines logo]()
$374
This Justfly.com deal was found by Cheapflights users on 6/9. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2512:20 pm
NAS
- ORD
1 stop12h 24m
JetBlue
Tue 7/287:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 6/9![JetBlue logo]()
$380
This Southwest deal was found by Cheapflights users on 6/7. 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 7/148:45 am
NAS
- MDW
1 stop8h 35m
Southwest
Sat 7/185:00 am
MDW
- NAS
1 stop6h 40m
Southwest
Deal found 6/7![Southwest logo]()
$382
This Delta deal was found by Cheapflights users on 6/10. 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 12/41:20 pm
NAS
- MDW
1 stop9h 50m
Delta
Tue 12/86:00 am
MDW
- NAS
1 stop8h 30m
Delta
Deal found 6/10![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 6/10. 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 12/41:00 pm
NAS
- ORD
2 stops11h 50m
Delta
Tue 12/87:10 am
ORD
- NAS
1 stop7h 20m
Delta
Deal found 6/10![Delta logo]()
$399
This American Airlines deal was found by Cheapflights users on 6/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:10 pm
NAS
- ORD
1 stop14h 43m
American Airlines
Wed 11/45:00 am
ORD
- NAS
1 stop7h 59m
American Airlines
Deal found 6/8![American Airlines logo]()
$413
Best flights from Nassau to ChicagoDiscover carefully curated flight deals from Nassau to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 12, 2026.
Discover carefully curated flight deals from Nassau to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 12, 2026.
This JetBlue deal was found by Cheapflights users on 6/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/412:30 pm
NAS
- ORD
1 stop12h 14m
JetBlue
Tue 12/87:00 am
ORD
- NAS
1 stop9h 21m
JetBlue
Deal found 6/10![JetBlue logo]()
$325
This Southwest deal was found by Cheapflights users on 6/7. 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 7/148:45 am
NAS
- MDW
1 stop8h 35m
Southwest
Sat 7/185:00 am
MDW
- NAS
1 stop6h 40m
Southwest
Deal found 6/7![Southwest logo]()
$382
This Delta deal was found by Cheapflights users on 6/10. 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 12/41:20 pm
NAS
- MDW
1 stop9h 50m
Delta
Tue 12/86:00 am
MDW
- NAS
1 stop8h 30m
Delta
Deal found 6/10![Delta logo]()
$399
This American Airlines deal was found by Cheapflights users on 6/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/310:32 am
NAS
- ORD
2 stops8h 58m
American Airlines
Sat 10/106:26 pm
ORD
- NAS
1 stop14h 34m
American Airlines
Deal found 6/9![American Airlines logo]()
$501
This United Airlines deal was found by Cheapflights users on 6/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/253:59 pm
NAS
- ORD
Nonstop3h 56m
United Airlines
Tue 7/2810:32 am
ORD
- NAS
Nonstop3h 25m
United Airlines
Deal found 6/9![United Airlines logo]()
$571
This JetBlue deal was found by Cheapflights users on 6/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1512:20 pm
NAS
- ORD
1 stop12h 24m
JetBlue
Sun 7/197:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 6/10![JetBlue logo]()
$344
This JetBlue deal was found by Cheapflights users on 6/8. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1612:20 pm
NAS
- ORD
1 stop12h 24m
JetBlue
Tue 7/217:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 6/8![JetBlue logo]()
$353
This Delta deal was found by Cheapflights users on 6/10. 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 12/41:00 pm
NAS
- ORD
2 stops11h 50m
Delta
Tue 12/87:10 am
ORD
- NAS
1 stop7h 20m
Delta
Deal found 6/10![Delta logo]()
$399
This Southwest deal was found by Cheapflights users on 6/8. 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 7/38:45 am
NAS
- MDW
1 stop8h 35m
Southwest
Tue 7/712:00 pm
MDW
- NAS
1 stop5h 35m
Southwest
Deal found 6/8![Southwest logo]()
$424
This JetBlue deal was found by Cheapflights users on 6/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1512:20 pm
NAS
- ORD
1 stop12h 24m
JetBlue
Thu 7/167:00 am
ORD
- NAS
1 stop5h 50m
JetBlue
Deal found 6/12![JetBlue logo]()
$370
This Southwest deal was found by Cheapflights users on 6/10. 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 7/238:45 am
NAS
- MDW
2 stops10h 00m
Southwest
Thu 7/3011:00 am
MDW
- NAS
1 stop6h 35m
Southwest
Deal found 6/10![Southwest logo]()
$477
This American Airlines deal was found by Cheapflights users on 6/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2512:29 pm
NAS
- ORD
Nonstop3h 47m
American Airlines
Tue 7/287:00 am
ORD
- NAS
Nonstop3h 29m
American Airlines
Deal found 6/8![American Airlines logo]()
$556
This Southwest deal was found by Cheapflights users on 6/8. 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 9/241:10 pm
NAS
- MDW
2 stops8h 00m
Southwest
Sun 9/275:10 am
MDW
- NAS
1 stop6h 05m
Southwest
Deal found 6/8![Southwest logo]()
$481
This JetBlue deal was found by Cheapflights users on 6/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:27 pm
NAS
- ORD
1 stop6h 17m
JetBlue
Sat 8/17:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 6/12![JetBlue logo]()
$442
This Southwest deal was found by Cheapflights users on 6/8. 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 10/282:10 pm
NAS
- MDW
1 stop7h 20m
Southwest
Wed 11/45:15 am
MDW
- NAS
1 stop6h 00m
Southwest
Deal found 6/8![Southwest logo]()
$518
This Southwest deal was found by Cheapflights users on 6/10. 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 7/158:45 am
NAS
- MDW
2 stops9h 20m
Southwest
Sat 7/186:35 am
MDW
- NAS
2 stops10h 55m
Southwest
Deal found 6/10![Southwest logo]()
$532
Last-minute flights from Nassau to ChicagoDiscover last-minute flight deals from Nassau to Chicago. Data last updated June 12, 2026 and is based on user searches.
Discover last-minute flight deals from Nassau to Chicago. Data last updated June 12, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 6/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/126:30 pm
NAS
- ORD
1 stop15h 30m
Air Canada
Mon 6/156:22 pm
ORD
- NAS
2 stops22h 08m
Air Canada
Deal found 6/7![Air Canada logo]()
$420
This Southwest deal was found by Cheapflights users on 6/8. 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 7/38:45 am
NAS
- MDW
1 stop8h 35m
Southwest
Tue 7/712:00 pm
MDW
- NAS
1 stop5h 35m
Southwest
Deal found 6/8![Southwest logo]()
$424
This Justfly.com deal was found by Cheapflights users on 6/10. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:27 pm
NAS
- ORD
1 stop6h 17m
JetBlue
Wed 7/157:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 6/10![JetBlue logo]()
$334
This JetBlue deal was found by Cheapflights users on 6/7. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:27 pm
NAS
- ORD
1 stop6h 17m
JetBlue
Sat 7/187:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 6/7![JetBlue logo]()
$325
This Southwest deal was found by Cheapflights users on 6/7. 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 7/148:45 am
NAS
- MDW
1 stop8h 35m
Southwest
Sat 7/185:00 am
MDW
- NAS
1 stop6h 40m
Southwest
Deal found 6/7![Southwest logo]()
$382
This JetBlue deal was found by Cheapflights users on 6/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1512:20 pm
NAS
- ORD
1 stop12h 24m
JetBlue
Thu 7/167:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 6/10![JetBlue logo]()
$324
This JetBlue deal was found by Cheapflights users on 6/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1512:20 pm
NAS
- ORD
1 stop12h 24m
JetBlue
Sun 7/197:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 6/10![JetBlue logo]()
$344
This deal was found by Cheapflights users on 6/12. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/153:02 pm
NAS
- ORD
1 stop9h 42m
JetBlue
Sat 7/187:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 6/12![JetBlue logo]()
$371
This Priceline deal was found by Cheapflights users on 6/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/152:35 pm
NAS
- ORD
2 stops18h 10m
Multiple Airlines
Sat 7/187:00 am
ORD
- NAS
1 stop9h 22m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$429
This Southwest deal was found by Cheapflights users on 6/10. 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 7/158:45 am
NAS
- MDW
1 stop8h 35m
Southwest
Thu 7/167:50 am
MDW
- NAS
2 stops9h 45m
Southwest
Deal found 6/10![Southwest logo]()
$455
This JetBlue deal was found by Cheapflights users on 6/8. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1612:20 pm
NAS
- ORD
1 stop12h 24m
JetBlue
Tue 7/217:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 6/8![JetBlue logo]()
$353
This Justfly.com deal was found by Cheapflights users on 6/9. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2512:20 pm
NAS
- ORD
1 stop12h 24m
JetBlue
Tue 7/287:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 6/9![JetBlue logo]()
$380
One-way flights from Nassau to ChicagoSearch for one-way flight options from Nassau to Chicago. Find affordable one-way fares based on user searches. Data last updated June 12, 2026.
Search for one-way flight options from Nassau to Chicago. Find affordable one-way fares based on user searches. Data last updated June 12, 2026.
This JetBlue deal was found by Cheapflights users on 6/8. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/812:20 pm
NAS
- ORD
1 stop12h 24m
JetBlue
Deal found 6/8![JetBlue logo]()
$216
This JetBlue deal was found by Cheapflights users on 6/8. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/512:20 pm
NAS
- ORD
1 stop12h 24m
JetBlue
Deal found 6/8![JetBlue logo]()
$235
This Southwest deal was found by Cheapflights users on 6/12. 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 7/158:45 am
NAS
- MDW
1 stop7h 30m
Southwest
Deal found 6/12![Southwest logo]()
$240
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/43:59 pm
NAS
- ORD
Nonstop3h 56m
United Airlines
Deal found 6/10![United Airlines logo]()
$248
This United Airlines deal was found by Cheapflights users on 6/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/92:35 pm
NAS
- ORD
1 stop18h 06m
United Airlines
Deal found 6/9![United Airlines logo]()
$253
This United Airlines deal was found by Cheapflights users on 6/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:53 pm
NAS
- ORD
1 stop9h 34m
United Airlines
Deal found 6/8![United Airlines logo]()
$258
This Delta deal was found by Cheapflights users on 6/9. 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 8/43:22 pm
NAS
- ORD
2 stops20h 20m
Delta
Deal found 6/9![Delta logo]()
$259
This JetBlue deal was found by Cheapflights users on 6/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/53:00 pm
NAS
- ORD
1 stop9h 44m
JetBlue
Deal found 6/11![JetBlue logo]()
$262
This Southwest deal was found by Cheapflights users on 6/8. 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 9/241:10 pm
NAS
- MDW
2 stops8h 50m
Southwest
Deal found 6/8![Southwest logo]()
$273
This Expedia deal was found by Cheapflights users on 6/7. 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.
Mon 8/36:30 pm
NAS
- ORD
2 stops26h 35m
Air Canada
Deal found 6/7![Air Canada logo]()
$277
This JetBlue deal was found by Cheapflights users on 6/8. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/73:00 pm
NAS
- ORD
1 stop9h 44m
JetBlue
Deal found 6/8![JetBlue logo]()
$287
This Southwest deal was found by Cheapflights users on 6/8. 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 8/271:10 pm
NAS
- MDW
1 stop9h 20m
Southwest
Deal found 6/8![Southwest logo]()
$290
Find flight deals from Nassau to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Nassau (NAS) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $324 (JetBlue) |
One-way from | $216 (JetBlue) |
Popular in | November |
Cheapest in | January |
Average price | $608 |
Good round-trip deal | $395 or less |
Good one-way deal | $223 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Nassau to Chicago 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 June 12, 2026.
Use the filters below to find and compare flights from Nassau to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
NassauChicago
NAS - ORD
NASORD
Nassau Intl
Fri 12/4
12:30 pm-11:44 pm
1 stop12h 14m
Chicago O'Hare Intl
Tue 12/8
7:00 am-5:21 pm
1 stop9h 21m
$325
NassauChicago
NAS - ORD
NASORD
Nassau Intl
Wed 7/15
12:20 pm-11:44 pm
1 stop12h 24m
Chicago O'Hare Intl
Sun 7/19
7:00 am-5:22 pm
1 stop9h 22m
$344
NassauChicago
NAS - ORD
NASORD
Nassau Intl
Thu 7/16
12:20 pm-11:44 pm
1 stop12h 24m
Chicago O'Hare Intl
Tue 7/21
7:00 am-5:22 pm
1 stop9h 22m
$353
NassauChicago
NAS - ORD
NASORD
Nassau Intl
Wed 7/15
12:20 pm-11:44 pm
1 stop12h 24m
Chicago O'Hare Intl
Thu 7/16
7:00 am-1:50 pm
1 stop5h 50m
$370
NassauChicago
NAS - MDW
NASMDW
Nassau Intl
Tue 7/14
8:45 am-4:20 pm
1 stop8h 35m
Chicago Midway
Sat 7/18
5:00 am-12:40 pm
1 stop6h 40m
$382
NassauChicago
NAS - MDW
NASMDW
Nassau Intl
Fri 12/4
1:20 pm-10:10 pm
1 stop9h 50m
Chicago Midway
Tue 12/8
6:00 am-3:30 pm
1 stop8h 30m
$399
NassauChicago
NAS - ORD
NASORD
Nassau Intl
Fri 12/4
1:00 pm-11:50 pm
2 stops11h 50m
Chicago O'Hare Intl
Tue 12/8
7:10 am-3:30 pm
1 stop7h 20m
$399
NassauChicago
NAS - MDW
NASMDW
Nassau Intl
Fri 7/3
8:45 am-4:20 pm
1 stop8h 35m
Chicago Midway
Tue 7/7
12:00 pm-6:35 pm
1 stop5h 35m
$424
NassauChicago
NAS - ORD
NASORD
Nassau Intl
Wed 7/29
6:27 pm-11:44 pm
1 stop6h 17m
Chicago O'Hare Intl
Sat 8/1
7:00 am-5:22 pm
1 stop9h 22m
$442
NassauChicago
NAS - MDW
NASMDW
Nassau Intl
Thu 7/23
8:45 am-5:45 pm
2 stops10h 00m
Chicago Midway
Thu 7/30
11:00 am-6:35 pm
1 stop6h 35m
$477
Showing 1-10 of 36 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on Nassau-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Nassau-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Nassau-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Nassau-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Nassau-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Nassau to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Nassau with our price prediction graph.
NAS-CHI
NAS-ORD
NAS-MDW
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 Nassau to Chicago
NAS-CHI
NAS-ORD
NAS-MDW
What is the cheapest month to book a flight from Nassau to Chicago?
Currently, December is the cheapest month in which you can book a flight from Nassau to Chicago (average of $209). Flying from Nassau to Chicago in June is currently the most expensive (average of $524). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from NAS to CHI?
Find hourly flight availability from Nassau to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2026.
When flying from Nassau to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Nassau to Chicago
Explore weekly flight availability from Nassau to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 12, 2026.
The most flights from NAS to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Nassau to Chicago?
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated June 12, 2026.
Read reviews from past customers who have flown Delta,United Airlines, andAmerican Airlines from Nassau to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.2
Comfort
7.8
Boarding
8.1
Crew
8.5
Overall
7.9
Entertainment
7.8
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Food
7.2
Comfort
7.8
Boarding
8.1
Crew
8.5
Overall
7.9
Entertainment
7.8
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Food
7.2
Comfort
7.8
Boarding
8.1
Crew
8.5
Overall
7.9
Entertainment
7.8
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Food
7.2
Comfort
7.8
Boarding
8.1
Crew
8.5
Overall
7.9
Entertainment
7.8
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Related info for your journey
Find useful and relevant information for your journey from Nassau to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Other flights to Chicago
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Nassau and Chicago flights
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Other flights from Nassau
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Popular flight searches
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Top 2 airlines flying from Nassau to Chicago
Discover the top 2 airlines that operate flights from Nassau to Chicago. 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 June 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$415 | Average$564 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$434 | Average$505 | FlexibilityNo cancel fee | On-time69% |