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$244+ 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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
NAS — CHI
Aug 24 — Aug 311
Mon 8/24
Mon 8/31
1 adult, Economy
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Cheap flight deals from Nassau to Chicago

Cheapest flights from Nassau to Chicago
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 July 25, 2026.

This Orbitz deal was found by Cheapflights users on 7/20. 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.
Fri 8/216:30 pm
NAS
-
ORD
1 stop26h 22m
Air Canada
Wed 8/268:40 am
ORD
-
NAS
1 stop27h 55m
Air Canada
Deal found 7/20$378
This Southwest deal was found by Cheapflights users on 7/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/101:10 pm
NAS
-
MDW
1 stop6h 55m
Southwest
Tue 9/156:15 am
MDW
-
NAS
1 stop5h 00m
Southwest
Deal found 7/23$380
This Expedia deal was found by Cheapflights users on 7/24. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:30 pm
NAS
-
ORD
1 stop26h 18m
Air Canada
Sun 9/278:40 pm
ORD
-
NAS
1 stop19h 50m
Air Canada
Deal found 7/24$393
This Air Canada deal was found by Cheapflights users on 7/20. 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 7/256:30 pm
NAS
-
ORD
1 stop15h 30m
Air Canada
Tue 7/283:40 pm
ORD
-
NAS
1 stop20h 55m
Air Canada
Deal found 7/20$401
This Air Canada deal was found by Cheapflights users on 7/20. 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 11/232:05 pm
NAS
-
ORD
1 stop25h 47m
Air Canada
Sat 11/283:45 pm
ORD
-
NAS
1 stop20h 30m
Air Canada
Deal found 7/20$402
This Air Canada deal was found by Cheapflights users on 7/25. 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.
Sat 10/36:30 pm
NAS
-
ORD
1 stop15h 30m
Air Canada
Sat 10/109:50 am
ORD
-
NAS
1 stop6h 40m
Air Canada
Deal found 7/25$405
This Air Canada deal was found by Cheapflights users on 7/24. 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.
Wed 10/212:35 pm
NAS
-
ORD
1 stop20h 42m
Air Canada
Mon 10/269:05 pm
ORD
-
NAS
1 stop13h 25m
Air Canada
Deal found 7/24$408
This Southwest deal was found by Cheapflights users on 7/22. 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.
Fri 8/211:10 pm
NAS
-
MDW
1 stop9h 20m
Southwest
Fri 8/287:55 pm
MDW
-
NAS
2 stops15h 35m
Southwest
Deal found 7/22$503
This Southwest deal was found by Cheapflights users on 7/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:10 pm
NAS
-
MDW
1 stop5h 50m
Southwest
Sun 8/238:45 pm
MDW
-
NAS
2 stops14h 30m
Southwest
Deal found 7/23$510
This Southwest deal was found by Cheapflights users on 7/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:10 pm
NAS
-
MDW
1 stop9h 25m
Southwest
Sun 9/275:15 am
MDW
-
NAS
1 stop6h 00m
Southwest
Deal found 7/24$521
This Delta deal was found by Cheapflights users on 7/21. 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.
Fri 9/253:18 pm
NAS
-
MDW
1 stop8h 26m
Delta
Mon 9/286:05 am
MDW
-
NAS
1 stop6h 48m
Delta
Deal found 7/21$567

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 July 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$378
(Orbitz)

One-way from

$244
(Expedia)

Popular in

August

Cheapest in

January

Average price

$469

Good round-trip deal

$311 or less

Good one-way deal

$212 or less
Provider with most accurate pricing for Nassau Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Nassau Intl-Chicago (CHI) flights.
Search Deals
From Nassau Intl to Chicago (CHI)
Search Deals
One-way flight from Nassau Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Nassau Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Nassau Intl to Chicago (CHI).
Search Deals

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 July 25, 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

Price

Cheapest round-trip
Quickest round-trip

NassauChicago

NAS - MDW

NASMDW

Nassau Intl

Thu 9/10

1:10 pm-7:05 pm

1 stop6h 55m

Chicago Midway

Tue 9/15

6:15 am-12:15 pm

1 stop5h 00m

$380

NassauChicago

NAS - ORD

NASORD

Nassau Intl

Fri 8/21

6:30 pm-2:44 pm

2 stops21h 14m

Chicago O'Hare Intl

Wed 8/26

3:45 pm-1:35 pm

2 stops20h 50m

$389

NassauChicago

NAS - ORD

NASORD

Nassau Intl

Fri 9/25

6:30 pm-7:48 pm

1 stop26h 18m

Chicago O'Hare Intl

Sun 9/27

8:40 pm-5:30 pm

1 stop19h 50m

$393

NassauChicago

NAS - ORD

NASORD

Nassau Intl

Sat 10/3

6:30 pm-9:00 am

1 stop15h 30m

Chicago O'Hare Intl

Sat 10/10

9:50 am-5:30 pm

1 stop6h 40m

$405

NassauChicago

NAS - ORD

NASORD

Nassau Intl

Mon 11/23

9:25 pm-2:52 pm

2 stops18h 27m

Chicago O'Hare Intl

Sat 11/28

7:05 am-8:25 pm

2 stops12h 20m

$418

NassauChicago

NAS - ORD

NASORD

Nassau Intl

Fri 9/25

6:30 pm-10:17 am

2 stops16h 47m

Chicago O'Hare Intl

Mon 9/28

9:50 am-5:30 pm

1 stop6h 40m

$421

NassauChicago

NAS - ORD

NASORD

Nassau Intl

Fri 8/21

6:30 pm-2:55 pm

1 stop21h 25m

Chicago O'Hare Intl

Fri 8/28

8:50 pm-5:30 pm

1 stop19h 40m

$424

NassauChicago

NAS - ORD

NASORD

Nassau Intl

Thu 9/10

2:20 pm-2:52 pm

1 stop25h 32m

Chicago O'Hare Intl

Tue 9/15

5:53 pm-1:25 pm

2 stops42h 32m

$436

NassauChicago

NAS - MDW

NASMDW

Nassau Intl

Fri 8/21

1:10 pm-9:30 pm

1 stop9h 20m

Chicago Midway

Fri 8/28

7:55 pm-12:30 pm

2 stops15h 35m

$503

NassauChicago

NAS - MDW

NASMDW

Nassau Intl

Fri 9/25

1:10 pm-9:35 pm

1 stop9h 25m

Chicago Midway

Sun 9/27

5:15 am-12:15 pm

1 stop6h 00m

$521

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/24

Showing 1-10 of 33 resultsSorted by cheapest first
1
2
3
4
  • 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.
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

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 November is currently the most expensive (average of $695). 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 July 25, 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 July 25, 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?

Airfare is below average for this route at the moment.
Nassau to Chicago flights typically cost between $498 and $683 in August.
The cheapest round-trip price found within the last 5 days was $378 on Air Canada (Aug 21-Aug 26).

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 July 25, 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.
Delta
7.8
Good
8,486 reviews

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

7.8

Overall

7.8

Reviews

1 / 20
8.0
Excellent

Rakshith,May 2026

TPE - SEA

I got middle seat, but it was cheap $340 for Taipei to PDX ,
Delta
7.8
Good
8,486 reviews
Delta
7.8
Good
8,486 reviews

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

7.8

Overall

7.8

Reviews

1 / 20
8.0
Excellent

Rakshith,May 2026

TPE - SEA

I got middle seat, but it was cheap $340 for Taipei to PDX ,
United Airlines
7.4
Good
10,034 reviews
Delta
7.8
Good
8,486 reviews

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

7.8

Overall

7.8

Reviews

1 / 20
8.0
Excellent

Rakshith,May 2026

TPE - SEA

I got middle seat, but it was cheap $340 for Taipei to PDX ,
American Airlines
7.1
Good
11,847 reviews
Delta
7.8
Good
8,486 reviews

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

7.8

Overall

7.8

Reviews

1 / 20
8.0
Excellent

Rakshith,May 2026

TPE - SEA

I got middle seat, but it was cheap $340 for Taipei to PDX ,

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.

  • What airport do you fly from for flights from Nassau to Chicago?

    If you book a flight to Chicago from Nassau, you will be flying from Intl, which is the city’s only airport. Nassau Intl (NAS) is located 7.0 mi from the center of Nassau. There are 2 flights from Intl to Chicago per day from 2 different airlines.

  • How long is the flight from Nassau to Chicago?

    There are many flights that can get you from Nassau to Chicago in 6h 55m. Fly via Southwest or Air Canada to get the fastest option. Airlines will cover a distance of 1297 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Nassau to Chicago round-trip?

    Flying on American Airlines is currently your cheapest option to Chicago, with prices starting at $359. Another option worth looking into is United Airlines, starting at $434 round trip. American Airlines is currently priced 36% below the average price you’ll pay for this route.

  • What are the most reliable airlines from Nassau to Chicago?

    Before booking your flight to Chicago from Nassau, check out the most reliable airlines to get you to your destination on time: American Airlines (93%), Qatar Airways (86%), United Airlines( 73%).

  • What are the cheapest flights from Nassau to Chicago?

    While on average a flight from Nassau to Chicago is generally $326, our data shows the cheapest flight currently is $190. When looking at the most popular route, (Nassau Intl - Chicago O'Hare Intl), you can expect to pay $433 for that flight.

  • Can I find deals for flights from Nassau to Chicago that include hotel bookings?

    Yes. In addition to deals on Nassau to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Nassau to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Nassau to Chicago.

  • Can I find deals for business class flights from Nassau to Chicago?

    Yes. Cheapflights offers flight deals from Nassau to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • 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 November is currently the most expensive (average of $695). 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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Alternative routes for Nassau to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Nassau to O'Hare Intl flights
Nassau to St. Louis flights

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 July 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$359Average$544FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$434Average$505FlexibilityNo cancel feeOn-time69%

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