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How to get fromClearwater to Chicagoby bus, plane, bus (Flixbus, Greyhound), train (Amtrak), car, or train

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There are 8 ways to get from Clearwater to Chicago by bus, plane, bus (Flixbus, Greyhound), train (Amtrak), car, or train

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Line 52 bus, line 300 bus to Tampa, fly to Chicago Midway International Airport

    best
    1. Take the bus from Park St Terminal - Platform - B to Psta 34Th St Complex - Shelter - Abus bus
    2. Take the bus from Psta 34Th St Layby - Platform - D to TPA RENTAL CAR FACILITY westboundbus bus
    3. Fly from Tampa (TPA) to Chicago Midway International Airport (MDW)plane plane TPA - MDW
    6h 48m
    $107–410

  2. Bus to Sarasota–Bradenton International Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from Psta Grand Central Station to Desoto Station Parking For 12 & 203bus bus
    2. Fly from Sarasota–Bradenton International Airport (SRQ) to Chicago O'Hare International Airport (ORD)plane plane SRQ - ORD
    9h 14m
    $77–381

  3. Bus

    1. Take the bus from Tampa Bus Station to Atlanta Bus Stationbus bus FlixBus N2467
    2. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus bus Greyhound US0100
    30h 1m
    $195–335

  4. Train (Amtrak)

    1. Take the train from Tampa to Chicago Union Stationtrain train Floridian
    41h 28m
    $1,014–1,675

  5. Drive  1,119.6 mi

    1. Drive from Clearwater to Chicagocar car 1,119.6 mi
    20h 43m
    $205–296

  6. Line 52 bus, line 300 bus to Tampa, fly to Chicago O'Hare International Airport

    1. Take the bus from Park St Terminal - Platform - B to Psta 34Th St Complex - Shelter - Abus bus
    2. Take the bus from Psta 34Th St Layby - Platform - D to TPA RENTAL CAR FACILITY westboundbus bus
    3. Fly from Tampa (TPA) to Chicago O'Hare International Airport (ORD)plane plane TPA - ORD
    7h 15m
    $97–310

  7. Line 52 bus, line 34 bus, bus to Sarasota–Bradenton International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Park St Terminal - Platform - B to Largo Transit Centerbus bus
    2. Take the bus from Largo Commons Walmart Shelter - A to Grand Central Station - Hbus bus
    3. Take the bus from Psta Grand Central Station to Desoto Station Parking For 12 & 203bus bus
    4. Fly from Sarasota–Bradenton International Airport (SRQ) to Chicago Midway International Airport (MDW)plane plane SRQ - MDW
    8h 41m
    $102–491

  8. Fly Tampa to General Mitchell International Airport, train

    1. Fly from Tampa (TPA) to General Mitchell International Airport (MKE)plane plane TPA - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    9h 16m
    $702–1,194

Clearwater to Chicago by bus

Calendar5Weekly Buses
Duration30h 1mAverage Duration
Ticket$195Cheapest Price
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Comparing Your Travel Options

Map of how to get from Clearwater to Chicago.ExpandLaunch map view
  • Distance: 1,036.6 mi
  • Duration: 6h 48m

What companies run services between Clearwater, FL, USA and Chicago, IL, USA?

You can take a bus from Park St Terminal - Platform - B to Chicago Bus Station via Psta 34Th St Layby - Platform - D, Marion Transit Parking Lot, Tampa Bus Station, and Atlanta Bus Station in around 30h 1m. Alternatively, Amtrak operates a train from Tampa to Chicago Union Station once daily. Tickets cost $950–1,600 and the journey takes 40h 56m.

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