Direct flights from Key West to Chicago

Did you mean Flights from Chicago to Key West?

Key West

United States

EYW

Key West International Airport

Chicago

United States

ORD

Chicago O'Hare International Airport

Route: Nonstop service available
Distance: 1,254 miles
Marketing airlines: 3 airlines
Aircraft: 5 aircraft types
Dates: Oct 24, 2026 – Oct 17, 2027

Observed award fares

A sample of one-way prices for one traveler from Roame’s fare cache. Points, fees, and seats describe the same observation. Availability can change; confirm with the loyalty program before transferring points.

Lowest price in this limited sample: 7,500 points + $25.00 for EYW → ORD, Economy, on 2026-11-04, booked with Alaska Atmos Rewards. This is an observed fare, not a guaranteed price or the lowest price across all dates and programs.

Departure window: 2026-10-23 – 2026-11-21.

EYW → ORDEconomy
AA3657
7,500 points+ $25.00
Departure
2026-11-04
Seats seen
9
Book with
Alaska Atmos Rewards
Observed (UTC)
2026-10-22 08:18
EYW → ORDEconomy
AA3585
7,500 points+ $25.00
Departure
2026-11-04
Seats seen
9
Book with
Alaska Atmos Rewards
Observed (UTC)
2026-10-22 08:18
EYW → ORDEconomy
AA3585
7,500 points+ $25.00
Departure
2026-11-05
Seats seen
9
Book with
Alaska Atmos Rewards
Observed (UTC)
2026-10-21 20:59
EYW → ORDEconomy
AA3657
7,500 points+ $25.00
Departure
2026-11-05
Seats seen
9
Book with
Alaska Atmos Rewards
Observed (UTC)
2026-10-21 20:59
EYW → ORDEconomy
AA3585
7,500 points+ $25.00
Departure
2026-11-11
Seats seen
9
Book with
Alaska Atmos Rewards
Observed (UTC)
2026-10-23 02:57
EYW → ORDEconomy
AA3585
7,500 points+ $25.00
Departure
2026-11-13
Seats seen
9
Book with
Alaska Atmos Rewards
Observed (UTC)
2026-10-23 00:39
EYW → ORDEconomy
AA3585
7,500 points+ $25.00
Departure
2026-11-19
Seats seen
9
Book with
Alaska Atmos Rewards
Observed (UTC)
2026-10-22 00:37
EYW → ORDFirst
AA3585
15,000 points+ $25.00
Departure
2026-11-04
Seats seen
9
Book with
Alaska Atmos Rewards
Observed (UTC)
2026-10-22 08:18
EYW → ORDFirst
AA3657
15,000 points+ $25.00
Departure
2026-11-04
Seats seen
4
Book with
Alaska Atmos Rewards
Observed (UTC)
2026-10-22 08:18
EYW → ORDFirst
AA3585
15,000 points+ $25.00
Departure
2026-11-11
Seats seen
9
Book with
Alaska Atmos Rewards
Observed (UTC)
2026-10-23 02:57
EYW → ORDFirst
AA3585
15,000 points+ $25.00
Departure
2026-11-13
Seats seen
3
Book with
Alaska Atmos Rewards
Observed (UTC)
2026-10-23 00:39
EYW → ORDFirst
AA3585
15,000 points+ $25.00
Departure
2026-11-19
Seats seen
9
Book with
Alaska Atmos Rewards
Observed (UTC)
2026-10-22 00:37

Key West to Chicago route overview

Key West International Airport (EYW) serves Key West; Chicago O'Hare International Airport (ORD) serves Chicago.

The airports are 1,254 miles apart by great-circle distance.

Roame's current schedule feed shows nonstop service from EYW to ORD.

Marketing airlines listed in the current schedule, including codeshare sellers, are American Airlines (AA), Air New Zealand (NZ) and United Airlines (UA). This list does not identify the operating airline for each flight; check the flight details before booking.

Published schedule dates span Oct 24, 2026 – Oct 17, 2027.

Marketing airlines on the Key West to Chicago route

These are marketing airlines, including codeshare sellers. This list does not identify the operating airline for each flight; check the flight details before booking.

American Airlines (AA)Codeshare only
Air New Zealand (NZ)Codeshare only

Airline alliance affiliations represented: Oneworld, Star Alliance

Aircraft flying from EYW to ORD

Frequently asked questions

Which airports serve the Key West to Chicago route?

Key West International Airport (EYW) is the origin airport and Chicago O'Hare International Airport (ORD) is the destination airport.

How far is Chicago from Key West?

EYW and ORD are approximately 1,254 miles apart by great-circle distance.

Are there direct flights from EYW to ORD?

Yes. Roame's current schedule feed shows nonstop service from EYW to ORD.

Which airlines market flights from EYW to ORD?

Which aircraft fly from EYW to ORD?

Aircraft listed in the current schedule include Boeing 737-700 / Boeing 737-700ER (73G), Embraer 170 (E70), Embraer 175 (short wing) (E75), Embraer 175 (long wing) (E7W) and JET.