American Airlines offers flights from Key West to Chicago, with nonstop or connecting service from Key West International Airport (EYW) to O'Hare International Airport (ORD). Travelers fly between these cities for business trips, family visits and short stays.
Compare fares and schedules and choose the option that fits your trip to Chicago (ORD). Prices and availability may change based on travel dates and demand.
Key West (EYW)to
Round trip
Economy
Key West (EYW)to
Round trip
Economy
Key West (EYW)to
Round trip
Economy
Key West (EYW)to
Round trip
Economy
Key West (EYW)to
Round trip
Economy
Key West (EYW)to
Round trip
Economy
Key West (EYW)to
Round trip
Economy
Key West (EYW)to
Round trip
Economy
*Fares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Some fares listed may include one or more connections that are Basic Economy, which class is subject to additional terms and conditions. Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Additional baggage fees and charges for optional products and services may apply.
Saving on flights
Finding lower fares often depends on timing, flexibility and travel demand. These tips can make it easier to compare options and identify flights that fit your plans.
Booking 1 to 3 months ahead can help you find lower fares on flights to Chicago.
Midweek flights, such as Tuesdays or Wednesdays, can sometimes offer lower fares.
Off-peak seasons tend to be more affordable. If travel demand is higher during holidays or major events, consider less busy times for lower fares.
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Before your flight
Review these tips to prepare for your trip and get ready for your departure.
When to arrive
Arrive at least 2 hours before domestic flights. For international travel, plan for 3 hours before departure.
Check-in
Check in online or on the American app to download your boarding pass or print it before you arrive.
Flight info
Check your terminal and gate before you go and watch for updates in the app or on airport displays.
Documents
Bring a valid ID to pass through security. Make sure your travel details match your identification.
Airport experience
Allow extra time to reach your gate and get through security before boarding begins.
Amenities
Many airports offer dining, charging stations and other services to help you prepare for your trip before boarding.
Airport information
American flies to O’Hare International Airport (ORD), located about 18 miles northwest of downtown Chicago. The airport offers convenient access to Chicago and the surrounding region.
Getting from the airport
Transportation options from ORD to downtown Chicago include public transit, taxi or rideshare, rental car or hotel shuttle.
For more transportation details, visit the official O’Hare International Airport website.
The Blue Line train connects ORD with downtown Chicago, with travel times of about 45 minutes.
Many hotels offer shuttle service to and from ORD.
Taxis and app-based rideshare services are available at designated pickup areas.
On-site rental car facilities offer options for travelers who prefer to drive.
Plan your visit
Chicago’s seasons each bring a new side to the city, from lively outdoor scenes to cultural highlights.
City parks and lakefront paths fill with activity and outdoor events return.
Changing leaves and neighborhood festivals create a vibrant atmosphere.
Beaches, concerts and street fairs draw crowds to every corner of the city.
Museums, theaters and local dining offer warmth and classic Chicago experiences.
Chicago’s skyline, lakefront and cultural institutions make it a world-class city for visitors. The city’s museums, historic sites and diverse neighborhoods offer something for everyone.
Upgrade options
Make your trip more comfortable with Main Cabin Extra. Discover how Main Cabin Extra can enhance your trip.
More space with seats at the front of the Main Cabin or in exit rows.
Preferred Group 5 boarding allows easier access to overhead bins.
Enjoy beer, wine and spirits on flights with full beverage service.
Quick answers
Use the fare calendar and flight search tools on this page to compare prices across different travel dates. Adjusting your departure or return date may help you find more flight options and fares that fit your budget.
AAdvantage® members can earn miles on eligible American Airlines flights. Miles can be used toward future travel, upgrades and other rewards. Learn more about the AAdvantage® program.
When planning your trip, consider travel dates, flight options and activities at your destination. This page includes helpful information to help you compare flights and start planning your visit.
Explore local attractions, dining, entertainment and other experiences highlighted on this page to help plan your visit.
