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Cheap flights from New York Newark to Chicago Midway

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Compare New York Newark to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

Book the best Chicago Midway fare with no extra fees

Flight deals from New York Newark to Chicago Midway

Looking for a cheap last-minute deal or the best round-trip flight from New York Newark to Chicago Midway? Find the lowest prices on one-way and round-trip tickets right here.
Chicago.C$216 per passenger.Departing Wed, Sep 10, returning Sat, Sep 13.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from New York Newark on Wed, Sep 10, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Sat, Sep 13, arriving in New York Newark.Price includes taxes and charges.From C$216, select.
Chicago.C$216 per passenger.Departing Sat, May 31, returning Fri, Jun 6.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from New York Newark on Sat, May 31, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Fri, Jun 6, arriving in New York Newark.Price includes taxes and charges.From C$216, select.
Chicago.C$216 per passenger.Departing Thu, Oct 2, returning Sat, Oct 4.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from New York Newark on Thu, Oct 2, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Sat, Oct 4, arriving in New York Newark.Price includes taxes and charges.From C$216, select.
Chicago.C$217 per passenger.Departing Wed, Oct 29, returning Mon, Nov 3.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from New York Newark on Wed, Oct 29, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Mon, Nov 3, arriving in New York Newark.Price includes taxes and charges.From C$217, select.
Chicago.C$217 per passenger.Departing Wed, Jul 9, returning Tue, Jul 22.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from New York Newark on Wed, Jul 9, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Tue, Jul 22, arriving in New York Newark.Price includes taxes and charges.From C$217, select.
Chicago.C$217 per passenger.Departing Tue, Aug 12, returning Tue, Aug 26.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from New York Newark on Tue, Aug 12, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Tue, Aug 26, arriving in New York Newark.Price includes taxes and charges.From C$217, select.
Chicago.C$217 per passenger.Departing Sat, Aug 23, returning Wed, Sep 3.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from New York Newark on Sat, Aug 23, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Wed, Sep 3, arriving in New York Newark.Price includes taxes and charges.From C$217, select.
Chicago.C$231 per passenger.Departing Wed, May 28, returning Sat, May 31.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from New York Newark on Wed, May 28, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Sat, May 31, arriving in New York Newark.Price includes taxes and charges.From C$231, select.

Find the cheapest month to fly from New York Newark to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like New York Newark to Chicago Midway flights are currently cheapest in September.
May
from C$231
Jun
from C$248
Jul
from C$217
Aug
from C$217
Sep
from C$216
Oct
from C$216
Nov
from C$273
Dec
from C$588
Jan
from C$315
Feb
from C$532
Mar
from C$368
Apr
Find prices

Direct flights from New York Newark to Chicago Midway

New York Newark to Chicago Midway: Alternative routes

Compare routes from New York Newark to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

New York to Chicago: Flight information

The things to know before you go.
Cheapest flight foundC$216
Cheapest month to flyOctober
Average flight time2 hrs, 25 mins
Most popular airlineUnited
Average flights per week1

Finding cheap flights from New York Newark to Chicago Midway: Frequently asked questions

The best price we found for a round-trip flight from New York Newark to Chicago Midway is C$216. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 25 minutes is the average flight time from New York Newark to Chicago Midway.
United flies direct from New York Newark to Chicago Midway.
There is one flight per week flying from New York Newark to Chicago Midway, as of May 2025.
The cheapest month to fly from New York Newark to Chicago Midway is usually May 2025.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from New York Newark Airport to Chicago Midway Airport on Thursday, October 2, 2025.
Yes – the average flight time is 2 hours and 25 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Delta offers the cheapest flight tickets to Chicago Midway.

Travelling from Newark Liberty International Airport (EWR) to Chicago Midway International Airport (MDW): what you need to know

  • Chicago is one hour behind New York and is in the UTC-5 timezone.

  • Leave enough time to catch your EWR to MDW flight. As a general rule, turn up two hours before international departures and an hour ahead for domestic flights.

  • Travelling during a peak month such as April? Major public holidays and other high seasons can result in longer lines and delays at airport checkpoints. Play things extra safe and arrive up to four hours ahead of an international flight and two hours before domestic departures.

  • Think about adding a stopover when booking your ticket from Newark Liberty International Airport to Chicago Midway International Airport. Just uncheck 'Direct flights only' to break up your journey, or enjoy a detour to a new and interesting place. Here are some options between EWR and MDW:

    • Pittsburgh International Airport

    • Cleveland Hopkins International Airport

    • Ronald Reagan National Airport

How to find the cheapest flights from Newark Liberty International Airport (EWR) to Chicago Midway International Airport (MDW)

  • Right now, C$108 is the cheapest price we've seen for a one-way Newark Liberty International Airport to Chicago Midway International Airport flight. The best price for a return plane ticket is C$216. Remember that fares can change due to availability at the time of booking.

  • Don't leave everything to the last moment. You're more likely to find cheap tickets from EWR to MDW if you book early. Airlines often offer some terrific early bird deals.

  • If you can be flexible with your trip dates, use the 'Whole month' search tool. It'll show you the lowest price in each month when looking for a flight from Newark Liberty International Airport to Chicago Midway International Airport.

  • Finding cheap flights from EWR to MDW couldn't be easier with Price Alerts. Simply set up one of these automatic alerts and we'll notify you as soon as a new deal comes up.

  • Tailor your flights with filters. Choose your ideal departure and arrival times, total journey duration and airlines. You can also sort the results by 'Best,' 'Fastest' or 'Cheapest' flights from Newark Liberty International Airport to Chicago Midway International Airport.

Handy information about Newark Liberty International Airport (EWR)

  • EWR is located at Building 1, Conrad Road.

  • 73.3% of flights taking off from Newark Liberty International Airport reach their destination on schedule.

  • Central New York to Newark Liberty International Airport is approximately 24 kilometres. Depending on traffic, it'll take you about 30 minutes to get there if you're driving, catching a cab or ride-sharing.

  • The journey when using public transport takes about 1 hour 10 minutes.

  • Catching an early flight from Newark Liberty International Airport to Chicago Midway International Airport? Avoid the hassle of rushing to the airport (and sneak in some extra precious sleep) by choosing one of these hotels near EWR:

Arriving at Chicago Midway International Airport (MDW)

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • MDW is located at 5700 South Cicero.

  • Chicago Midway International Airport to central Chicago has a drive time of around 20 minutes. It's approximately 19 kilometres away.

  • Travelling to the centre on public transport takes roughly 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

  • It's time to pick your travel dates for your flight from Newark Liberty International Airport to Chicago Midway International Airport. July is the busiest month to visit Chicago. If you want a quieter vibe, go in May.

  • Lock in your flight from Newark Liberty International Airport to Chicago Midway International Airport for July if you'd like to visit Chicago during its warmest month. You can expect temperatures of between 15ºC (59ºF) and 29ºC (84ºF).

  • January sees average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Look for cheap tickets from EWR to MDW around that time if you like travelling in cooler conditions.

Explore more of United States

  • You've done Chicago, now it's time to discover other parts of United States. Travel about 451 kilometres south-east to Columbus to tick off its must-visit sights. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, there's plenty to keep you busy.

  • Indianapolis is another must-experience destination in United States and is around 257 kilometres south-east of Chicago. No trip is complete without a visit to The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

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Plan the rest of your trip from New York to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.