$246+ Cheap flights from Nassau (NAS) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/21. Fares are subject to change and may not be available on all flights or dates of travel.
NAS — CHI
Nov 25 — Dec 21
Round-trip
1 adult, Economy
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Find cheap flights from Nassau to Chicago with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Nassau to Chicago
Cheapest
Best
Last-minute
One-way
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 October 26, 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 October 26, 2026.
This Trip.com deal was found by Cheapflights users on 10/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/79:25 pm -
1 stop19h 13m
Mon 12/148:50 pm -
1 stop22h 35m
Deal found 10/22![Air Canada logo]()
$408
This Air Canada deal was found by Cheapflights users on 10/24. 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.
Sat 11/212:05 pm -
1 stop25h 57m
Sat 11/283:40 pm -
1 stop20h 35m
Deal found 10/24![Air Canada logo]()
$442
This Air Canada deal was found by Cheapflights users on 10/21. 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.
Mon 11/239:25 pm -
1 stop12h 58m
Sat 11/283:40 pm -
1 stop20h 35m
Deal found 10/21![Air Canada logo]()
$447
This Trip.com deal was found by Cheapflights users on 10/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2512:30 pm -
1 stop28h 08m
Sun 2/148:50 pm -
1 stop22h 35m
Deal found 10/25![Air Canada logo]()
$478
This American Airlines deal was found by Cheapflights users on 10/23. 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 11/2511:49 am -
1 stop9h 10m
Sun 2/148:20 am -
Nonstop3h 28m
Deal found 10/23![American Airlines logo]()
$502
This American Airlines deal was found by Cheapflights users on 10/23. 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.
Thu 12/1010:22 am -
1 stop9h 03m
Thu 12/179:33 pm -
1 stop10h 49m
Deal found 10/23![American Airlines logo]()
$506
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/1412:09 pm -
1 stop9h 02m
Wed 11/188:15 am -
1 stop8h 36m
Deal found 10/21![American Airlines logo]()
$511
This Mytrip deal was found by Cheapflights users on 10/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/78:30 am -
1 stop9h 46m
Mon 12/145:02 pm -
2 stops20h 43m
Deal found 10/22![Multiple Airlines logo]()
$588
This Delta deal was found by Cheapflights users on 10/21. 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 11/144:58 pm -
1 stop6h 56m
Wed 11/186:00 am -
1 stop8h 33m
Deal found 10/21![Delta logo]()
$702
This Delta deal was found by Cheapflights users on 10/23. 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.
Mon 11/234:58 pm -
1 stop6h 56m
Sat 11/286:00 am -
1 stop6h 50m
Deal found 10/23![Delta logo]()
$717
This Southwest deal was found by Cheapflights users on 10/22. 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.
Mon 12/71:10 pm -
2 stops10h 30m
Mon 12/148:50 pm -
2 stops14h 25m
Deal found 10/22![Southwest logo]()
$734
This Delta deal was found by Cheapflights users on 10/21. 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.
Thu 11/121:18 pm -
1 stop10h 36m
Mon 11/236:00 am -
1 stop4h 53m
Deal found 10/21![Delta logo]()
$1,192
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 October 26, 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 October 26, 2026.
This Air Canada deal was found by Cheapflights users on 10/24. 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.
Mon 11/239:25 pm -
2 stops18h 37m
Sat 11/281:55 pm -
1 stop22h 20m
Deal found 10/24![Air Canada logo]()
$450
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Thu 2/412:00 pm -
2 stops12h 46m
Sun 2/78:47 pm -
1 stop18h 28m
Deal found 10/25![Multiple Airlines logo]()
$534
This Southwest deal was found by Cheapflights users on 10/25. 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 2/41:55 pm -
2 stops10h 05m
Sun 2/79:35 pm -
2 stops14h 25m
Deal found 10/25![Southwest logo]()
$577
This United Airlines deal was found by Cheapflights users on 10/21. 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 12/194:00 pm -
Nonstop4h 00m
Sun 12/209:35 pm -
1 stop13h 24m
Deal found 10/21![United Airlines logo]()
$612
This JetBlue deal was found by Cheapflights users on 10/25. 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 11/1212:21 pm -
1 stop12h 15m
Mon 11/237:00 am -
1 stop9h 25m
Deal found 10/25![JetBlue logo]()
$615
This Delta deal was found by Cheapflights users on 10/21. 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 11/144:58 pm -
1 stop6h 56m
Wed 11/186:00 am -
1 stop8h 33m
Deal found 10/21![Delta logo]()
$702
This JetBlue deal was found by Cheapflights users on 10/22. 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 11/142:56 pm -
1 stop9h 40m
Wed 11/187:00 am -
1 stop5h 51m
Deal found 10/22![JetBlue logo]()
$615
This United Airlines deal was found by Cheapflights users on 10/23. 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 4/12:53 pm -
1 stop17h 54m
Mon 4/55:45 pm -
1 stop19h 02m
Deal found 10/23![United Airlines logo]()
$617
This Delta deal was found by Cheapflights users on 10/25. 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.
Mon 11/234:58 pm -
1 stop6h 56m
Sat 11/286:00 am -
1 stop6h 50m
Deal found 10/25![Delta logo]()
$717
This Southwest deal was found by Cheapflights users on 10/22. 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.
Mon 12/71:10 pm -
2 stops10h 30m
Mon 12/148:50 pm -
2 stops14h 25m
Deal found 10/22![Southwest logo]()
$734
Last-minute flights from Nassau to ChicagoDiscover last-minute flight deals from Nassau to Chicago. Data last updated October 26, 2026 and is based on user searches.
Discover last-minute flight deals from Nassau to Chicago. Data last updated October 26, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 10/21. 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.
Thu 11/121:18 pm -
1 stop10h 36m
Mon 11/236:00 am -
1 stop4h 53m
Deal found 10/21![Delta logo]()
$1,192
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/1412:09 pm -
1 stop9h 02m
Wed 11/188:15 am -
1 stop8h 36m
Deal found 10/21![American Airlines logo]()
$511
This Delta deal was found by Cheapflights users on 10/21. 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 11/144:58 pm -
1 stop6h 56m
Wed 11/186:00 am -
1 stop8h 33m
Deal found 10/21![Delta logo]()
$702
This Air Canada deal was found by Cheapflights users on 10/24. 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.
Sat 11/212:05 pm -
1 stop25h 57m
Sat 11/283:40 pm -
1 stop20h 35m
Deal found 10/24![Air Canada logo]()
$442
This Air Canada deal was found by Cheapflights users on 10/21. 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.
Mon 11/239:25 pm -
1 stop12h 58m
Sat 11/283:40 pm -
1 stop20h 35m
Deal found 10/21![Air Canada logo]()
$447
This Delta deal was found by Cheapflights users on 10/23. 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.
Mon 11/234:58 pm -
1 stop6h 56m
Sat 11/286:00 am -
1 stop6h 50m
Deal found 10/23![Delta logo]()
$717
This WestJet deal was found by Cheapflights users on 10/23. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/235:05 pm -
2 stops25h 59m
Sat 11/286:44 pm -
2 stops20h 31m
Deal found 10/23![WestJet logo]()
$3,341
This Trip.com deal was found by Cheapflights users on 10/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2512:30 pm -
1 stop28h 08m
Sun 2/148:50 pm -
1 stop22h 35m
Deal found 10/25![Air Canada logo]()
$478
This American Airlines deal was found by Cheapflights users on 10/23. 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 11/2511:49 am -
1 stop9h 10m
Sun 2/148:20 am -
Nonstop3h 28m
Deal found 10/23![American Airlines logo]()
$502
This Air Canada deal was found by Cheapflights users on 10/25. 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 11/272:05 pm -
2 stops18h 49m
Sun 2/211:55 pm -
1 stop22h 20m
Deal found 10/25![Air Canada logo]()
$521
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 October 26, 2026.
Search for one-way flight options from Nassau to Chicago. Find affordable one-way fares based on user searches. Data last updated October 26, 2026.
This American Airlines deal was found by Cheapflights users on 10/21. 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 12/2112:32 pm -
Nonstop3h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$246
This Trip.com deal was found by Cheapflights users on 10/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/262:05 pm -
1 stop22h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Air Canada logo]()
$250
This Trip.com deal was found by Cheapflights users on 10/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:25 pm -
1 stop21h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Air Canada logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 11/105:30 pm -
2 stops25h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 11/105:30 pm -
2 stops26h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$276
This Orbitz deal was found by Cheapflights users on 10/21. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:30 pm -
1 stop8h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Air Canada logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 1/204:54 pm -
1 stop17h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$278
This Justfly.com deal was found by Cheapflights users on 10/24. 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.
Sun 11/83:25 pm -
1 stop28h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Air Canada logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 1/207:45 am -
3 stops17h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 10/24. 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.
Mon 11/99:25 am -
2 stops33h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Multiple Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 1/512:00 pm -
2 stops49h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Multiple Airlines logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/64:54 pm -
2 stops24h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$299
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 October 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $386 (Kiwi.com) |
One-way from | $246 (American Airlines) |
Popular in | March |
Cheapest in | January |
Average price | $472 |
Good one-way deal | $346 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 7,457,451 searches. Data last updated October 26, 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 Nassau Intl - ORD Chicago O'Hare Intl
NASORD
Nassau Intl
Tue 11/10
12:30 pm-3:38 pm
1 stop28h 08m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$255
NassauChicago
NAS Nassau Intl - ORD Chicago O'Hare Intl
NASORD
Nassau Intl
Mon 12/7
12:30 pm-3:38 pm
1 stop28h 08m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$255
NassauChicago
NAS Nassau Intl - ORD Chicago O'Hare Intl
NASORD
Nassau Intl
Mon 11/9
9:25 pm-5:43 pm
1 stop21h 18m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$255
NassauChicago
NAS Nassau Intl - MDW Chicago Midway
NASMDW
Nassau Intl
Tue 11/10
5:30 pm-5:47 pm
2 stops25h 17m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$265
NassauChicago
NAS Nassau Intl - ORD Chicago O'Hare Intl
NASORD
Nassau Intl
Wed 11/4
12:30 pm-6:30 pm
2 stops31h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$282
NassauChicago
NAS Nassau Intl - ORD Chicago O'Hare Intl
NASORD
Nassau Intl
Wed 1/20
4:00 pm-11:50 am
2 stops20h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$286
NassauChicago
NAS Nassau Intl - MDW Chicago Midway
NASMDW
Nassau Intl
Wed 1/6
4:54 pm-4:26 pm
2 stops24h 32m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$299
NassauChicago
NAS Nassau Intl - ORD Chicago O'Hare Intl
NASORD
Nassau Intl
Thu 12/31
11:17 am-5:59 pm
1 stop7h 42m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$306
NassauChicago
NAS Nassau Intl - MDW Chicago Midway
NASMDW
Nassau Intl
Mon 11/9
5:30 pm-11:22 am
3 stops18h 52m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$336
NassauChicago
NAS Nassau Intl - MDW Chicago Midway
NASMDW
Nassau Intl
Mon 12/7
5:30 pm-11:33 am
2 stops19h 03m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$337
Showing 1-10 of 31 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, February is the cheapest month in which you can book a flight from Nassau to Chicago (average of $452). Flying from Nassau to Chicago in March is currently the most expensive (average of $640). 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.
How much does it cost to fly round-trip from Nassau to Chicago?
Airfare is below average for this route at the moment.
Nassau to Chicago flights typically cost between $442 and $584 in February.The cheapest round-trip price found within the last 5 days was $386 on Multiple Airlines (Feb 4-Feb 7).
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 October 26, 2026.
Read reviews from past customers who have flown United Airlines and American 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.
Comfort
7.3
Entertainment
7.1
Food
6.7
Overall
7.3
Crew
8.1
Boarding
7.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Comfort
7.3
Entertainment
7.1
Food
6.7
Overall
7.3
Crew
8.1
Boarding
7.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Comfort
7.3
Entertainment
7.1
Food
6.7
Overall
7.3
Crew
8.1
Boarding
7.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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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 7,457,451 searches. Data last updated October 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$352 | Average$581 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$434 | Average$524 | FlexibilityNo cancel fee | On-time69% |