Direct flights from Chicago to Key West

Did you mean Flights from Key West to Chicago?

Chicago

United States

ORD

Chicago O'Hare International Airport

Key West

United States

EYW

Key West International Airport

Route: Nonstop service available
Distance: 1,254 miles
Marketing airlines: 3 airlines
Aircraft: 6 aircraft types
Dates: Nov 2, 2026 – Oct 31, 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 ORD → EYW, Economy, on 2026-11-17, 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: 2026-11-12 – 2026-12-11.

ORD → EYWEconomy
AA3657
7,500 points+ $25.00
Departure
2026-11-17
Seats seen
9
Book with
Alaska Atmos Rewards
Observed (UTC)
2026-11-10 15:32
ORD → EYWEconomy
AA3585
7,500 points+ $25.00
Departure
2026-11-17
Seats seen
8
Book with
Alaska Atmos Rewards
Observed (UTC)
2026-11-10 15:32
ORD → EYWFirst
AA3657
15,000 points+ $25.00
Departure
2026-11-17
Seats seen
6
Book with
Alaska Atmos Rewards
Observed (UTC)
2026-11-10 15:32
ORD → EYWFirst
AA3585
15,000 points+ $25.00
Departure
2026-11-17
Seats seen
7
Book with
Alaska Atmos Rewards
Observed (UTC)
2026-11-10 15:32
ORD → EYWEconomy
UA3487
19,000 points+ $9.00
Departure
2026-11-29
Seats seen
9
Book with
Virgin Australia
Observed (UTC)
2026-11-10 19:25
ORD → EYWEconomy
UA3689
19,000 points+ $9.00
Departure
2026-12-09
Seats seen
9
Book with
Virgin Australia
Observed (UTC)
2026-11-12 09:57
ORD → EYWEconomy
UA3689
19,000 points+ $9.00
Departure
2026-12-11
Seats seen
5
Book with
Virgin Australia
Observed (UTC)
2026-11-11 16:57

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Transfer partners in our directory: Marriott Bonvoy, Choice Privileges, IHG Rewards, Accor Live Limitless. Check current eligibility and terms before transferring.

Chicago to Key West route overview

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

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

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

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 Nov 2, 2026 – Oct 31, 2027.

Marketing airlines on the Chicago to Key West 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.

Air New Zealand (NZ)Codeshare only

Airline alliance affiliations represented: Oneworld, Star Alliance

Aircraft flying from ORD to EYW

Frequently asked questions

Which airports serve the Chicago to Key West route?

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

How far is Key West from Chicago?

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

Are there direct flights from ORD to EYW?

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

Which airlines market flights from ORD to EYW?

Which aircraft fly from ORD to EYW?

Aircraft listed in the current schedule include Boeing 737-800 (738), Boeing 737-700 / Boeing 737-700ER (73G), Embraer 170 (E70), Embraer 175 (short wing) (E75), Embraer 175 (long wing) (E7W) and JET.