What is the cheapest way to get from Chicago to Oldsmar?

The cheapest way to get from Chicago to Oldsmar is to drive which costs $200 - $300 and takes 20h 19m.

What is the fastest way to get from Chicago to Oldsmar?

The fastest way to get from Chicago to Oldsmar is to fly which takes 6h 17m and costs $120 - $650.

Is there a direct train between Chicago and Oldsmar?

No, there is no direct train from Chicago station to Oldsmar. However, there are services departing from Chicago Union Station and arriving at Tampa via . The journey, including transfers, takes approximately 41h 11m.

How far is it from Chicago to Oldsmar?

The distance between Chicago and Oldsmar is 1033 miles. The road distance is 1127.8 miles.

How do I travel from Chicago to Oldsmar without a car?

The best way to get from Chicago to Oldsmar without a car is to bus and taxi which takes 33h 40m and costs $380 - $600.

How long does it take to get from Chicago to Oldsmar?

It takes approximately 6h 17m to get from Chicago to Oldsmar, including transfers.

Where do I catch the Chicago to Oldsmar train from?

Chicago to Oldsmar train services, operated by Amtrak, depart from Chicago Union Station.

Train or fly from Chicago to Oldsmar?

The best way to get from Chicago to Oldsmar is to fly which takes 6h 17m and costs $120 - $650. Alternatively, you can train, which costs $600 - $1,300 and takes 41h 11m.

What is the time difference between Chicago and Oldsmar?

Oldsmar is 1h ahead of Chicago. It is currently 8:59 PM in Chicago and 9:59 PM in Oldsmar.

Where does the Chicago to Oldsmar train arrive?

Chicago to Oldsmar train services, operated by Amtrak, arrive at Tampa station.

Can I drive from Chicago to Oldsmar?

Yes, the driving distance between Chicago to Oldsmar is 1128 miles. It takes approximately 20h 19m to drive from Chicago to Oldsmar.

Where can I stay near Oldsmar?

There are 2124+ hotels available in Oldsmar.

Chicago to Oldsmar - 6 ways to travel via train, plane, bus, taxi, and car

How to get fromChicago to Oldsmar

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There are 6 ways to get from Chicago to Oldsmar by plane, bus, taxi, 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.

Fly from Chicago Midway International Airport
best
1. Fly from Chicago Midway International Airport (MDW) to Tampa (TPA)plane MDW - TPA
6h 17m
$128–610
Bus, taxi
1. Take the bus from Chicago Bus Station to Atlanta Bus Stationbus
2. Take the bus from Atlanta Bus Station to La Grange Bus Stationbus
3. Take the bus from La Grange Bus Station to Mobilebus
4. Take the bus from Loxley to Ruskinbus
5. Take the taxi from Ruskin to Oldsmartaxi
33h 40m
$380–561
Train (Amtrak)
1. Take the train from Chicago Union Station to Tampatrain Floridian
41h 11m
$639–1,230
Drive 1,121.2 mi
1. Drive from Chicago to Oldsmarcar 1,121.2 mi
20h 19m
$205–296
Fly from Chicago O'Hare International Airport
1. Fly from Chicago O'Hare International Airport (ORD) to Tampa (TPA)plane ORD - TPA
6h 45m
$158–560
Train to General Mitchell International Airport, fly
1. Take the train from Chicago Union Station to Milwaukeetrain
2. Fly from General Mitchell International Airport (MKE) to Tampa (TPA)plane MKE - TPA
7h 55m
$185–774

Chicago Midway International Airport (MDW) to Tampa (TPA) flights

44Weekly Planes

2h 59mAverage Duration

$126Cheapest Price

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Questions & Answers

Map of how to get from Chicago to Oldsmar.

Launch map view

Distance: 1,027.1 mi
Duration: 6h 17m

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

Southwest Airlines, Delta, and Frontier Airlines fly from Chicago Midway International Airport (MDW) to Tampa (TPA) every 4 hours. Alternatively, Amtrak operates a train from Chicago Union Station to Tampa once daily. Tickets cost $550–1,200 and the journey takes 40h 47m.

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