Bus Tickets from Key West, FL to Chicago, IL

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TodayMay 6
TomorrowMay 7
ThuMay 8
FriMay 9
SatMay 10
from US$165
SunMay 11
MonMay 12
TueMay 13

Cheap buses leaving Saturday

One passenger / one way

  • This trip is recommended because it is the: 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:

Last refresh of the prices: Yesterday at 7:56 PM EDT.

Prices and availability are subject to change.

Accepted payments

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Bus Key West to Chicago: Trip Overview

Average Ticket PriceUS$270
Average Bus Trip Duration1d 16h
Number of daily buses6
Earliest bus departure10:00am
Distance1999 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 travelling 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 on the trip Key West - Chicago

  1. How long is the bus trip from Key West to Chicago?

    The bus ride from Key West to Chicago takes 1d 16h, on average. If you're looking for the fastest way to get there, you'll find a bus doing the trip in about 1d 11h.

  2. How far is Key West from Chicago?

    The distance between Key West and Chicago is around 2000 km (1240 miles).

  3. What are the departure and arrival locations for buses traveling from Key West to Chicago?

    Buses traveling this route start their trip at Caroline St, in Key West, and end it at Downtown Greyhound Station, in Chicago.

  4. What is the cheapest way to go from Key West to Chicago?

    Taking the bus is the cheapest option to travel from Key West to Chicago. Starting at US$165, this bus is the most cost-effective option for your journey.

  5. How much does it cost to take the bus from Key West to Chicago?

    The bus fare from Key West to Chicago is approximately US$270.

  6. Can I take an overnight bus from Key West to Chicago?

    Yes! Catch buses leaving from Key West until 5:00pm and reaching Chicago on the following day.

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
US$260
05-05
No data
Today
No data
05-07
No data
05-08
No data
05-09
No data
05-10
US$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 US$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 US$158 to US$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 US$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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