New York Chicago
New York to Chicago is the second-busiest air corridor in the country, with nonstop flights leaving from three New York airports most hours of the day.
If you are in Manhattan and heading to the Loop or Chicago's west side, fly LaGuardia to Midway on Southwest. Both airports sit closer to their city centers than any other pairing on this route. Midway's Orange Line drops you in the Loop in 25 minutes. The flight runs about two and a half hours, with departures throughout the day.
If you are going to O'Hare or anywhere on the north side, LaGuardia to O'Hare gives you Delta, American, United, and Spirit, with flights leaving about every hour. Newark to O'Hare has the same carriers at the same pace, so if you are in New Jersey or lower Manhattan, start there. The Blue Line from O'Hare takes about 45 minutes to the Loop.
Spirit flies the cheapest fares from both LaGuardia and Newark to O'Hare. You lose seat selection and carry-on bags, but the base fare can be half what the legacy carriers charge.
JFK to O'Hare is worth knowing about for one reason: JetBlue flies the Airbus A220-300 here, which has wider economy seats and bigger windows than anything else on a domestic flight this short. Delta, American, and Frontier also cover it.
If you see Turkish Airlines, Cathay Pacific, or Qantas on a JFK to O'Hare search, that is not their plane. Those are codeshare tickets that put you on an American or Delta flight with American or Delta crew. The only reason to book through them is if your frequent flyer program makes the math work.
Have a specific need? Use the decision guide below to filter by your airline, where you live, lounges, or where you're staying in Chicago.
Pick What Matters to You
Best pair by where you're coming from
Best pair by where you're staying in Chicago
Which pair your airline flies nonstop
| Airline | LGA–ORD | EWR–ORD | JFK–ORD | LGA–MDW |
|---|---|---|---|---|
| Cathay Pacific | — | — | ✓ | — |
| Frontier | — | — | ✓ | — |
| Turkish Airlines | — | — | ✓ | — |
| GoJet Airlines | — | ✓ | — | — |
| JetBlue | — | — | ✓ | — |
| Sun Country Airlines | — | ✓ | — | — |
| American Airlines | ✓ | ✓ | ✓ | — |
| United Airlines | ✓ | ✓ | — | — |
| Spirit Airlines | ✓ | ✓ | — | — |
| Qantas | — | — | ✓ | — |
| Delta Air Lines | ✓ | ✓ | ✓ | — |
| Southwest Airlines | — | — | — | ✓ |
Ranked by on-time performance
Lounge access by airport and terminal
Ranked by flights per week
Getting to the airport
Red-eye vs daytime departures
Premium cabin options
Connecting through New York from a domestic flight
Every New York airport has nonstop flights to Chicago throughout the day. A connection through a third city adds hours to a flight that takes under three. The only time it makes sense is if you are starting from a smaller city and connecting through a New York airport anyway.
New York & Chicago Airport Profiles
Each airport has a personality. Terminal quality, transit access, lounge scene, and crowd levels vary dramatically — sometimes more than the flight itself.
New York Metro
LaGuardia is the New York airport that does not pretend to be anything more than a domestic terminal. No international flights, no customs hall, no transatlantic gates competing for security lane capacity. The result is a faster, simpler airport experience than JFK or Newark for any flight that stays in the country. Eight miles from midtown Manhattan, it is also the closest major airport to the city center.
The rebuilt Terminal B replaced what was widely considered the worst major terminal in the country. The new building is bright and open, with real restaurants instead of the food court that used to define LaGuardia dining. Gates connect via an elevated pedestrian bridge with a clear sightline to the Manhattan skyline. Terminal C is equally compact. Neither terminal is large, and gate-to-gate walks stay under ten minutes.
Newark Liberty has three terminals, and Terminal A opened as a full rebuild in 2023. The old Terminal A was demolished and replaced, and the difference is dramatic. Terminal C is United's hub, massive and busy, with most international flights departing from here. Terminal B handles most other carriers.
The AirTrain connects all three terminals and the NJ Transit / Amtrak rail station. Unlike JFK, the terminals are closer together and the AirTrain loop is faster. Security at Terminal C can back up during afternoon and evening international departures.
The airport sits in New Jersey, around 10 miles from Manhattan. That proximity is deceptive because the drive crosses the Hudson via the Newark Bay or Lincoln Tunnel, and both can be brutal during peak hours. NJ Transit from Penn Station is the more reliable option.
JFK spreads across four active passenger terminals connected by the AirTrain, and walking between them is not an option. Terminal 1 is the old international building. Terminal 4 is the largest, handling most international carriers. Terminal 5 is the former TWA terminal, now JetBlue's home, with the mid-century curves still intact. Terminal 8 belongs to American and British Airways.
The terminal you depart from depends entirely on your airline. Security wait times vary between them. Terminal 4 tends to be the slowest during evening international departures. Terminal 8 has improved since the co-location of its two main carriers. The TWA Hotel sits adjacent to Terminal 5 if you need to sleep before an early departure or after a late arrival.
JFK feels enormous because it is. Budget extra time for the AirTrain if you are connecting between terminals or arriving by subway. The AirTrain loop takes 10 to 15 minutes end to end.
Chicago Metro
O'Hare has four terminals: Terminal 1, Terminal 2, Terminal 3, and the international Terminal 5. There is no Terminal 4. The terminals spread across a wide footprint connected by the ATS train and underground walkways. Allow 15 to 20 minutes to move between them.
Terminal 5 sits apart from the domestic terminals and handles most international flights. The ATS train connects it to the rest of the airport. Afternoon peaks bring longer security and immigration lines. The terminal is functional and recently updated, but smaller than the domestic concourses.
Terminals 1, 2, and 3 form the domestic core, with more dining and lounge options. The Blue Line train to downtown stops under Terminal 2, accessible from any terminal via the ATS.
Midway is a single-terminal airport on Chicago's southwest side, compact enough to walk end to end in around 10 minutes. One central security checkpoint feeds all concourses. Lines move faster than at larger airports, though holiday weekends and spring break mornings back up. The terminal is older but functional, with food and shops on both sides of security.
Gates are close together and boarding areas are small. Delays mean crowded gate areas with limited seating. The airport handles a high volume of traffic relative to its size. Expect an efficient, basic terminal where everything is a short walk.
Rockford is a small regional airport about 63 miles northwest of downtown Chicago. One terminal with a handful of gates. Security lines are short, and the walk from the parking lot to any gate takes a few minutes. The terminal is quiet outside of departure times, with limited food options.
Parking is close to the building and inexpensive. The trade-off is the drive from the Chicago metro area, which runs 60 to 90 minutes on I-90 depending on traffic and weather.
Which Airlines Fly Which Pairs
American Airlines and Delta Air Lines and United Airlines serve both LGA and EWR to ORD — airport flexibility on the New York side.
Not all planes are the same size. The aircraft type below each checkmark tells you whether you are getting a widebody (777, 787, A350) with wider seats and a quieter ride, or a narrowbody (737, A321) with a single aisle. On flights over five hours, the difference is significant.
737-800, 737 MAX 8
A319, 737-800
A319, 737 MAX 8
A220-300
74Y
A220-300, 737-800
CRJ-900, E175
A321neo
737-800, 737 MAX 8
A321neo, 737-900
737, 737-800
CR7
A320
A320
74Y
737-800
77X