Cheap flights from Key West (EYW) to Chicago (CHI) from $150

This is the cheapest one-way flight price, found on 9/20. Prices may vary by date and flight preferences.
EYW — CHI
Sep 26 — Oct 31

The best prices from Key West to Chicago are usually found in January or October, booked 38 days in advance, depart on a Tuesday or Monday and return on a Tuesday

How to find the cheapest flight from Key West (EYW) to Chicago (CHI)

All the information you need to plan the best EYW to CHI flight in 2023: compare Key West to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.

Popular in

April

Cheapest in

January

Round-trip from

$207

One-way from

$150
High demand for flights, 67% potential price rise
Best time to find cheap flights, 46% potential price drop
From Key West to Chicago (CHI)
One-way flight from Key West to Chicago (CHI)

EYW - CHI

Price

$207 - $364

CHI

Temperature

23 - 73.4 °F

CHI

Rainfall

1.7 - 4.9 inches

What is the cheapest day to fly round-trip from Key West to Chicago?

Wednesday is generally a great day to depart. Flying on this day could help you save up to 37%.

How far in advance should I book a flight from Key West to Chicago?

Travelers have found it’s best to book a flight 38 days in advance to save up to 76% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 38 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Key West to Chicago 1-2 weeks in advance for as low as $544, or $820 for flights within the next 24 hours.

What is the cheapest month to fly from Key West to Chicago?

January can be a great time to fly to Chicago from Key West with a flight ticket averaging about $597. Cheapflights users have found deals in the month of January for as cheap as $241. The most expensive prices can be found in the month of April.

When is the cheapest time to fly from Key West to Chicago (EYW - CHI)?

A simple way to save on the total cost of your ticket is to fly from Key West to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 27% on your trip compared to booking a flight in the morning.

Cheap American Airlines flights from Key West to Chicago

Find some of the cheapest American Airlines flights traveling from Key West to Chicago. Make sure to double check the flight details before booking.

Cheap United Airlines flights from Key West to Chicago

Browse through some of the cheapest United Airlines flights traveling from Key West to Chicago. Check back soon if you're not seeing flights that suit your needs.

Cheap Key West to Chicago flights in September & October 2023

The best prices found for EYW to CHI flights for September, October
These are some of the best deals we've found on flights to Chicago in 2023 at this time. Check back soon for alternative fares.

Key West to Chicago 2023 flight deals

Cheap flights to Chicago from Key West found for this year
These are some of the best deals we've found on flights to Chicago in 2023 at this time. Check back soon for alternative fares.

Non-stop flights to Chicago from Key West

Save time with Key West to Chicago direct flight deals
For a quicker trip, book one of these direct flights from Key West to Chicago. Users seeking other options on flights from Key West to Chicago should update the search form at the top of the page.

One-way flights to Chicago from Key West

The cheapest one-way flights from Key West to Chicago
Take a look at some of the best available options we've come across on one-way flights from Key West to Chicago. For those needing a return trip from Key West, there is a search form available above.

Find flights from Key West to Chicago within your budget

Use the slider to find flights from Key West to Chicago that fit your budget.

Fly from

Any airport

Fly to

Any airport

Budget

$208 - $418

Route

Depart

Return

Price

Key WestChicago O'Hare Intl

EYW - ORD

EYWORD

Key West

Thu 1/11

Nonstop3h 27m

Chicago O'Hare Intl

Mon 1/15

Nonstop3h 13m

Key WestChicago O'Hare Intl

EYW - ORD

EYWORD

Key West

Thu 1/11

1 stop5h 15m

Chicago O'Hare Intl

Mon 1/15

Nonstop3h 13m

Key WestChicago O'Hare Intl

EYW - ORD

EYWORD

Key West

Thu 1/11

1 stop5h 07m

Chicago O'Hare Intl

Mon 1/15

1 stop7h 06m

Key WestChicago Midway

EYW - MDW

EYWMDW

Key West

Thu 1/11

1 stop4h 47m

Chicago Midway

Mon 1/15

1 stop5h 51m

Key WestChicago Midway

EYW - MDW

EYWMDW

Key West

Fri 1/12

1 stop18h 01m

Chicago Midway

Mon 1/15

1 stop17h 10m

Key WestChicago O'Hare Intl

EYW - ORD

EYWORD

Key West

Tue 10/31

1 stop8h 25m

Chicago O'Hare Intl

Thu 11/2

1 stop6h 51m

Key WestChicago O'Hare Intl

EYW - ORD

EYWORD

Key West

Tue 10/31

1 stop8h 25m

Chicago O'Hare Intl

Thu 11/2

2 stops13h 45m

Key WestChicago O'Hare Intl

EYW - ORD

EYWORD

Key West

Fri 1/12

2 stops19h 53m

Chicago O'Hare Intl

Mon 1/15

1 stop8h 15m

Key WestChicago O'Hare Intl

EYW - ORD

EYWORD

Key West

Thu 1/11

2 stops9h 59m

Chicago O'Hare Intl

Mon 1/15

1 stop8h 15m

Flights are sorted by cheapest first

Deals found on 9/21

Reviews of airlines servicing Chicago

Read reviews from past customers who have flown American Airlines, United Airlines and Delta from Key West to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
3,016 reviews

Comfort

7.9

Food

7.2

Crew

8.5

Entertainment

7.8

Boarding

8.0

Overall

7.9

Reviews

1 / 10

The seats were wayyyy too small! If you are a larger person buying 2 seats would not work as arm rests do not go up

Delta
7.9
Good
3,016 reviews
Delta
7.9
Good
3,016 reviews

Comfort

7.9

Food

7.2

Crew

8.5

Entertainment

7.8

Boarding

8.0

Overall

7.9

Reviews

1 / 10

The seats were wayyyy too small! If you are a larger person buying 2 seats would not work as arm rests do not go up

Allegiant Air
7.5
Good
103 reviews
Delta
7.9
Good
3,016 reviews

Comfort

7.9

Food

7.2

Crew

8.5

Entertainment

7.8

Boarding

8.0

Overall

7.9

Reviews

1 / 10

The seats were wayyyy too small! If you are a larger person buying 2 seats would not work as arm rests do not go up

United Airlines
7.4
Good
1,888 reviews
Delta
7.9
Good
3,016 reviews

Comfort

7.9

Food

7.2

Crew

8.5

Entertainment

7.8

Boarding

8.0

Overall

7.9

Reviews

1 / 10

The seats were wayyyy too small! If you are a larger person buying 2 seats would not work as arm rests do not go up

American Airlines
7.2
Good
2,635 reviews
Delta
7.9
Good
3,016 reviews

Comfort

7.9

Food

7.2

Crew

8.5

Entertainment

7.8

Boarding

8.0

Overall

7.9

Reviews

1 / 10

The seats were wayyyy too small! If you are a larger person buying 2 seats would not work as arm rests do not go up

Related info for your journey

Useful info, stats and facts about Key West to Chicago flights.

What airport do you fly from for flights from Key West to Chicago?

Most people fly from Key West (EYW) if they book a flight from Key West to Chicago. On average, Key West has 3 outbound flights to Chicago per day from 3 airlines. Key West is conveniently located just 2.6 mi from Key West’s city center.

Can I find flights from Key West to Chicago for under $300 on Cheapflights?

Yes, there are multiple flights from Key West to Chicago for under $300. The cheapest flight booked recently is on American Airlines for just $208, but on average you can expect to pay $410.

Are there nonstop flights from Key West to Chicago for under $300 on Cheapflights?

Cheapflights has at least 1 direct flight from Key West to Chicago under $300. A good price for a nonstop flight from Key West to Chicago is less than $208.

What are the cheapest airlines flying from Key West to Chicago round-trip?

Flying on American Airlines is currently your cheapest option to Chicago, with prices starting at $208. Additional round-trip tickets that might be worth considering are offered by Delta and United Airlines, with the lowest prices starting at $227 and $364, respectively. American Airlines is priced at 65% lower than the current average price of a flight leaving 3 months from now.

What are the most popular routes from Key West to Chicago?

What are the most popular airlines that fly from Key West to Chicago?

What are the cheapest flights from Key West to Chicago?

Looking for the cheapest flight from Key West to Chicago? While on average our users pay $313, our data indicates the cheapest price to be $252. The most popular route (Key West - Chicago O'Hare Intl), is priced around $227.

What does EYW to ORD mean?

EYW and ORD are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. EYW to ORD refers to a flight route from Key West Airport to Chicago O'Hare Intl Airport. This flight route has multiple associated airports, so we think it might be helpful to learn the name and codes of them as well. They are Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

Top 3 airlines flying from Key West to Chicago

The chart below displays the airlines Cheapflights users traveling from Key West to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$226Average$355FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
DeltaCheapest$226Average$327FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapest$312Average$553FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

Weekly flight availability from Key West to Chicago

See how many times per day planes take to the skies headed from Key West to Chicago
Sunday3daily flights
Monday3daily flights
Tuesday3daily flights
Wednesday3daily flights
Thursday3daily flights
Friday3daily flights
Saturday3daily flights
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