Bus Tickets from Key West, FL to Chicago, IL

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TodayMay 6
TomorrowMay 7
ThuMay 8
FriMay 9
SatMay 10
from $158
SunMay 11
MonMay 12
TueMay 13

Cheap buses leaving Saturday

One passenger / one way

  • This trip is recommended because it is: Cheapest + Fastest
    Departure time: May 10 at
    Departure city: Key West
    Departure location: Key West Bus Station
    Arrival time: May 11 at
    Destination city: Chicago
    Destination location: Downtown Greyhound Station
    Operated by: Greyhound Lines, Inc.Greyhound Lines, Inc.
    Vehicle: BusDuration:
  • Departure time: May 10 at
    Departure city: Key West
    Departure location: Key West Bus Station
    Arrival time: May 12 at
    Destination city: Chicago
    Destination location: Downtown Greyhound Station
    Operated by: Greyhound Lines, Inc.Greyhound Lines, Inc.
    Vehicle: BusDuration:
  • Departure time: May 10 at
    Departure city: Key West
    Departure location: Key West Bus Station
    Arrival time: May 12 at
    Destination city: Chicago
    Destination location: 537-517 W. Jackson Blvd
    Operated by: Greyhound Lines, Inc.Greyhound Lines, Inc.
    Vehicle: BusDuration:
  • Departure time: May 10 at
    Departure city: Key West
    Departure location: Key West Bus Station
    Arrival time: May 11 at
    Destination city: Chicago
    Destination location: Chicago 95Th & Dan Ryan
    Operated by: Greyhound Lines, Inc.Greyhound Lines, Inc.
    Vehicle: BusDuration:

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Bus Key West to Chicago: Trip Overview

Average ticket price$270
Average bus trip duration1d 16h
Number of daily buses6
Earliest bus departure10:00am
Distance1240 miles (1999 km)
Latest bus departure5:00pm

Key West to Chicago Bus

Busbud shows you the best bus ticket fares and bus schedules so you can easily plan and book a trip by bus from Key West to Chicago.

Bus service from Key West to Chicago will be provided by the most trusted bus companies.

From cheap bus tickets to more luxurious buses traveling from Key West to Chicago, we offer a wide range of bus services to best suit your needs depending on how much your budget is.

Frequently asked questions for your trip Key West - Chicago

Find cheapest prices for buses

Price is for a one-way ticket for one passenger and based on past searches.

Best price found
05/04
$260
05/05
No data
Today
No data
05/07
No data
05/08
No data
05/09
No data
05/10
$158
05/11
No data
busbud logoThe cheapest trip from Key West to Chicago was searched and found on May 10, 2025 with a price of $158

To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Key West to Chicago, as early as possible.

You can expect to pay from $158 to $349 for a bus ticket from Key West to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $158 which is on 2025-05-10.

About Bus Travel

Bus Travel Tips

If you're abroad, study some local language. Not only could it get you out of a pickle during your bus trip from Key West to Chicago but it'll also be endearing to native speakers who will surely appreciate your effort.

Much more than a mere vehicle taking you from Key West to Chicago, riding the bus will expose you to some of the most stunning panoramas while enroute to your final bus stop.

Taking the bus creates the smallest carbon footprint compared to other modes of transport. Not to mention that buses will allow you to discover scenic gems from Key West to Chicago that are otherwise impossible to come by with a plane.

Make a music playlist for your bus ride from Key West to Chicago, and enjoy the scenery to tunes from your own personal soundtrack.

Did you know?

The word 'bus' is an abbreviation of 'omnibus" which means 'for all' in Latin as buses were meant to be transportation for everybody.

9.2% of ground transportation in Europe is done by bus versus 7.4% by train.

The bus driver with the longest career in the world drove more than 2,000,000 miles and is a happy World Record holder.

Will you be returning to Key West by bus?

Bus from Key West to Chicago

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