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$324+ Cheap flights from Manhattan (MHK) 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 6/5. Fares are subject to change and may not be available on all flights or dates of travel.
MHK — CHI
Jun 7 — Jun 141
Sun 6/7
Sun 6/14
1 adult, Economy
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Cheap flight deals from Manhattan to Chicago

Cheapest flights from Manhattan to Chicago
Explore the most affordable flight options available from Manhattan to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 8, 2026.

This American Airlines deal was found by Cheapflights users on 5/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/34:55 pm
MHK
-
ORD
Nonstop2h 04m
American Airlines
Tue 7/76:04 am
ORD
-
MHK
1 stop5h 16m
American Airlines
Deal found 5/7$448
This American Airlines deal was found by Cheapflights users on 5/6. 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 6/134:55 pm
MHK
-
ORD
Nonstop2h 04m
American Airlines
Wed 6/242:26 pm
ORD
-
MHK
Nonstop1h 58m
American Airlines
Deal found 5/6$449
This American Airlines deal was found by Cheapflights users on 5/5. 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.
Tue 6/26:51 am
MHK
-
ORD
Nonstop1h 59m
American Airlines
Tue 6/95:00 am
ORD
-
MHK
1 stop6h 19m
American Airlines
Deal found 5/5$478
This American Airlines deal was found by Cheapflights users on 5/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/264:56 pm
MHK
-
ORD
Nonstop2h 04m
American Airlines
Sat 6/272:27 pm
ORD
-
MHK
Nonstop1h 58m
American Airlines
Deal found 5/7$480
This American Airlines deal was found by Cheapflights users on 5/4. 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.
Tue 5/197:04 am
MHK
-
ORD
Nonstop2h 01m
American Airlines
Sat 5/239:06 pm
ORD
-
MHK
Nonstop1h 57m
American Airlines
Deal found 5/4$487
This American Airlines deal was found by Cheapflights users on 5/6. 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 6/134:55 pm
MHK
-
ORD
Nonstop2h 04m
American Airlines
Thu 6/255:00 am
ORD
-
MHK
1 stop6h 19m
American Airlines
Deal found 5/6$489

Find flight deals from Manhattan to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Manhattan (MHK) 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 May 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$448
(American Airlines)

One-way from

$324
(American Airlines)

Good round-trip deal

$497 or less

Good one-way deal

$435 or less
Provider with most accurate pricing for Manhattan-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Manhattan-Chicago (CHI) flights.
Search Deals
From Manhattan to Chicago (CHI)
Search Deals
One-way flight from Manhattan to Chicago (CHI)
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Price to beat on a round-trip flight from Manhattan to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Manhattan to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Manhattan 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 May 8, 2026.
Use the filters below to find and compare flights from Manhattan to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ManhattanChicago

MHK - ORD

MHKORD

Manhattan

Sat 6/13

4:55 pm-6:59 pm

Nonstop2h 04m

Chicago O'Hare Intl

Wed 6/24

5:59 am-11:19 am

1 stop5h 20m

$458
Quickest round-trip

ManhattanChicago

MHK - ORD

MHKORD

Manhattan

Wed 6/3

6:51 am-8:50 am

Nonstop1h 59m

Chicago O'Hare Intl

Wed 6/10

2:26 pm-4:24 pm

Nonstop1h 58m

$468

ManhattanChicago

MHK - ORD

MHKORD

Manhattan

Fri 6/26

4:56 pm-7:00 pm

Nonstop2h 04m

Chicago O'Hare Intl

Sat 6/27

2:27 pm-4:25 pm

Nonstop1h 58m

$480

ManhattanChicago

MHK - ORD

MHKORD

Manhattan

Sat 6/13

4:55 pm-6:59 pm

Nonstop2h 04m

Chicago O'Hare Intl

Thu 6/25

5:00 am-11:19 am

1 stop6h 19m

$489
Cheapest one-way

ManhattanChicago

MHK - ORD

MHKORD

Manhattan

Thu 5/28

6:00 am-9:34 pm

2 stops15h 34m

$341

ManhattanChicago

MHK - ORD

MHKORD

Manhattan

Sun 5/31

6:48 pm-7:27 am

2 stops12h 39m

$385

ManhattanChicago

MHK - ORD

MHKORD

Manhattan

Sat 5/30

6:48 pm-10:33 am

2 stops15h 45m

$393

ManhattanChicago

MHK - ORD

MHKORD

Manhattan

Fri 5/29

6:48 pm-8:49 am

2 stops14h 01m

$394

ManhattanChicago

MHK - ORD

MHKORD

Manhattan

Wed 10/28

6:00 am-9:30 pm

2 stops15h 30m

$413

ManhattanChicago

MHK - ORD

MHKORD

Manhattan

Tue 10/27

6:44 pm-9:10 am

2 stops14h 26m

$416

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/7

Showing 1-10 of 14 resultsSorted by cheapest first
1
2

Compare providers for flights from Manhattan to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Manhattan to Chicago in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Manhattan-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Manhattan-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Manhattan-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Manhattan-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 Manhattan-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 Manhattan to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Manhattan 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 Manhattan to Chicago

What is the cheapest time of day to fly from MHK to CHI?

Find hourly flight availability from Manhattan 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 May 8, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Manhattan to Chicago as you normally would.

Weekly flight availability from Manhattan to Chicago

Explore weekly flight availability from Manhattan 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 May 8, 2026.

The most flights from MHK to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (5 on average).

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 May 8, 2026.
Read reviews from past customers who have flown American Airlines from Manhattan 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.
American Airlines
7.1
Good
11,667 reviews

Comfort

7.2

Crew

7.9

Entertainment

6.9

Food

6.4

Overall

7.1

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!
American Airlines
7.1
Good
11,667 reviews
American Airlines
7.1
Good
11,667 reviews

Comfort

7.2

Crew

7.9

Entertainment

6.9

Food

6.4

Overall

7.1

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!

Related info for your journey

Find useful and relevant information for your journey from Manhattan 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 Manhattan to Chicago?

    Manhattan (MHK) is the airport you will fly out of if you book a flight from Manhattan to Chicago. You should not have trouble finding flights to Chicago from Manhattan; the airport handles an average of 5 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 1 airline has flights from the Manhattan airport to Chicago. It is only a 6.2 mi journey to Manhattan (MHK) from Manhattan’s city center.

  • How long is the flight from Manhattan to Chicago?

    Departing from Manhattan to Chicago will take you 2h 04m. The distance between Manhattan and Chicago is about 500 mi. All flights are typically nonstop.

  • What is the cheapest airline to fly from Manhattan to Chicago round-trip?

    Flying on American Airlines is currently your cheapest option to Chicago, with prices starting at $361.

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

    No one likes to see their flight delayed. When booking a flight from Manhattan to Chicago consider choosing British Airways (83%), Qatar Airways (77%) or American Airlines (71%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Manhattan to Chicago?

    Looking at all options, your cheapest flight can be booked for $289. While the most popular route (Manhattan - Chicago O'Hare Intl) can be booked for $448 on average, our data indicates $1,296 when flying from Manhattan to Chicago.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Manhattan 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.

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
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Manhattan to Chicago

Discover the top airline that operate flights from Manhattan 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 May 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$361Average$490FlexibilityNo cancel feeOn-time71%

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