Cheap flight deals from Manhattan to Chicago Starting at $401

We've found these cheap flights for you. You can book one-way or round-trip flight tickets.

Round-trip
One way

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

When is the cheapest time to fly from Manhattan to Chicago?

We monitor flight fares to help you find the best deals effortlessly

Cheapest flights

From price

16 23
23 30
Apr

30 6
6 13
13 20
20 27
May

27 4
4 11
11 18
18 25
Jun

25 1
1 8

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

When are flight tickets from Manhattan (MHK) to Chicago (CHI) the cheapest?

Airlines adjust prices for flights from Manhattan to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much do flights from Manhattan (MHK) to Chicago (CHI) cost?

According to Trip.com's data, the lowest price is around $433.
How long does it take to fly from Manhattan (MHK) to Chicago (CHI) and what is the distance?

It takes around 1 hour 49 minutes to fly from Manhattan (MHK) to Chicago (CHI).
What is the transportation method from the main airport to downtown in Chicago?
- The distance from O'Hare Intl. Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
- The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.
What are the most popular airlines that fly from Manhattan (MHK) to Chicago (CHI)?

Airlines with flights from Manhattan (MHK) to Chicago (CHI): American Airlines, Qatar Airways and British Airways.

How to find a cheap flight from Manhattan to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Manhattan to Chicago. Book your flights at the right time and save more.

Be flexible with your travel dates to get the cheapest Manhattan to Chicago ticket.

Tap "Date" in the flight search bar to browse the calendar and find airfare from Manhattan to Chicago for the next six months in 2025. If you're looking to fly within the next three months, the lowest fare is $401 for a one-way ticket on Sun, May 11.

Compare cheap Manhattan to Chicago flight deals from hundreds of airlines.

Our powerful search system compares prices from over 500 airlines. So you can find the cheapest flights from Manhattan to Chicago. The most affordable airline currently operating on this route is American Airlines.

Set up a Price Alert to track fare drops.

Set up a Price Alert for your Manhattan to Chicago route to track ticket prices effortlessly—no need to check manually every day.

Don't miss out on cheap Manhattan to Chicago flight deals and promo codes.

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Book early or wait unitl the last minute to fine the best fares.

It's always better to book early! Airlines typically release their lowest fares about a year before departure, so check as soon as flights become available. If you miss that window, you may still find great deals closer to your travel date.

Search for flights on the go.

For the best booking experience on the go, download Trip.com and search for cheap flights from Manhattan to Chicago to access exclusive deals just for you.

Flight Info | Manhattan to Chicago

Cheapest nonstop flight price	$400
Cheapest round-trip ticket price	$432
Off-season for travel	January
Peak season for travel	March
Flight distance	821.11 km
Average flight time	1 hour 49 minutes
Popular airline	American Airlines