There are 7 ways to get from Chicago to Oldsmar by plane, bus (Greyhound, Flixbus), train (Amtrak), car, train, subway, or bus
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly Chicago Midway International Airport to Tampa
best- Fly from Chicago Midway International Airport (MDW) to Tampa (TPA)plane MDW - TPA
6h 17m$108–410Bus
- Take the bus from Chicago Bus Station to Atlanta Bus Stationbus Greyhound US0100
- Take the bus from Atlanta Bus Station to Tampa Bus Stationbus FlixBus N2467
28h 50m$202–327Train (Amtrak)
- Take the train from Chicago Union Station to Tampatrain Floridian
41h 11m$1,039–1,584Drive 1,119.7 mi
- Drive from Chicago to Oldsmarcar 1,119.7 mi
20h 19m$205–296Fly Chicago O'Hare International Airport to Tampa
- Fly from Chicago O'Hare International Airport (ORD) to Tampa (TPA)plane ORD - TPA
6h 43m$118–390Train to General Mitchell International Airport, fly to Tampa
- Take the train from Chicago Union Station to Milwaukeetrain
- Fly from General Mitchell International Airport (MKE) to Tampa (TPA)plane MKE - TPA
7h 56m$704–1,191Subway to Chicago Midway International Airport, fly to Sarasota–Bradenton International Airport, line 203 bus, line 18 bus, line 62 bus, line 78 bus
- Take the subway from Adams/Wabash to Midwaysubway
- Fly from Chicago Midway International Airport (MDW) to Sarasota–Bradenton International Airport (SRQ)plane MDW - SRQ
- Take the bus from Downtown Station to Psta Grand Central Stationbus
- Take the bus from Grand Central Station - C to Tyrone Square Mall Shelter - Bbus
- Take the bus from Tyrone Square Mall Shelter - C to Main St + Pine Tree Lnbus
- Take the bus from Main St + Pine Tree Ln to Tampa Rd + Pinckney Stbus
9h 50m$124–624
Chicago to Oldsmar by bus
Comparing Your Travel Options
The cheapest way to get from Chicago to Oldsmar is to fly which costs $100 - $410 and takes 6h 17m.
The fastest way to get from Chicago to Oldsmar is to fly which takes 6h 17m and costs $100 - $410.
No, there is no direct bus from Chicago station to Oldsmar. However, there are services departing from Chicago Bus Station and arriving at Tampa Rd & Commerce Blvd via Atlanta Bus Station, Marion Transit Center and North West Transfer Center Tampa. The journey, including transfers, takes approximately 28h 50m.
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.
The distance between Chicago and Oldsmar is 1033 miles. The road distance is 1126.3 miles.
The best way to get from Chicago to Oldsmar without a car is to bus which takes 28h 50m and costs $200 - $330.
It takes approximately 6h 17m to get from Chicago to Oldsmar, including transfers.
Chicago to Oldsmar bus services, operated by Greyhound USA, depart from Chicago Bus Station.
Chicago to Oldsmar train services, operated by Amtrak, depart from Chicago Union Station.
The best way to get from Chicago to Oldsmar is to fly which takes 6h 17m and costs $100 - $410. Alternatively, you can bus, which costs $200 - $330 and takes 28h 50m, you could also train, which costs $1,000 - $1,600 and takes 41h 11m.
What companies run services between Chicago, IL, USA and Oldsmar, FL, USA?
Southwest Airlines and Delta fly from Chicago Midway International Airport (MDW) to Tampa (TPA) every 4 hours. Alternatively, you can take a bus from Chicago Bus Station to Tampa Rd & Commerce Blvd via Atlanta Bus Station, Marion Transit Center, and North West Transfer Center Tampa in around 28h 50m.
- Website
- southwest.com
Flights from Chicago Midway International Airport to Tampa
- Ave. Duration
- 2h 34m
- When
- Every day
- Estimated price
- $130–700
Flights from Chicago Midway International Airport to Tampa via Nashville
- Ave. Duration
- 4h 12m
- When
- Every day
- Estimated price
- $130–700
Flights from General Mitchell International Airport to Tampa
- Ave. Duration
- 2h 42m
- When
- Every day
- Estimated price
- $150–750
Flights from General Mitchell International Airport to Tampa via Chicago Midway International Airport
- Ave. Duration
- 4h 22m
- When
- Saturday
- Estimated price
- $150–750
Flights from General Mitchell International Airport to Tampa via St. Louis
- Ave. Duration
- 4h 28m
- When
- Tuesday, Wednesday, and Sunday
- Estimated price
- $160–800
Flights from General Mitchell International Airport to Tampa via Nashville
- Ave. Duration
- 4h 36m
- When
- Monday, Thursday, Friday, Tuesday, Wednesday, and Sunday
- Estimated price
- $150–750
Flights from Chicago Midway International Airport to Sarasota–Bradenton International Airport
- Ave. Duration
- 2h 39m
- When
- Every day
- Estimated price
- $110–600
Flights from Chicago Midway International Airport to Sarasota–Bradenton International Airport via Nashville
- Ave. Duration
- 4h 47m
- When
- Thursday, Sunday, Monday, Friday, Tuesday, and Wednesday
- Estimated price
- $120–600
Flights from Chicago Midway International Airport to Sarasota–Bradenton International Airport via Orlando
- Ave. Duration
- 5h 30m
- When
- Sunday, Tuesday, Wednesday, Monday, Thursday, and Friday
- Estimated price
- $120–600
- Website
- delta.com
Flights from Chicago Midway International Airport to Tampa via Atlanta
- Ave. Duration
- 4h 27m
- When
- Every day
- Estimated price
- $130–700
Flights from Chicago O'Hare International Airport to Tampa via Atlanta
- Ave. Duration
- 4h 42m
- When
- Every day
- Estimated price
- $85–440
Flights from General Mitchell International Airport to Tampa via Detroit
- Ave. Duration
- 4h 40m
- When
- Every day
- Estimated price
- $160–800
Flights from General Mitchell International Airport to Tampa via Atlanta
- Ave. Duration
- 4h 41m
- When
- Every day
- Estimated price
- $150–750
Flights from Chicago Midway International Airport to Sarasota–Bradenton International Airport via Atlanta
- Ave. Duration
- 5h 19m
- When
- Every day
- Estimated price
- $110–600
- Website
- united.com
Flights from Chicago O'Hare International Airport to Tampa
- Ave. Duration
- 2h 55m
- When
- Every day
- Estimated price
- $85–440
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Tampa
- Ave. Duration
- 2h 50m
- When
- Every day
- Estimated price
- $85–440
Flights from Chicago O'Hare International Airport to Tampa via Nashville
- Ave. Duration
- 4h 55m
- When
- Every day
- Estimated price
- $85–440
- Website
- flyfrontier.com
Flights from Chicago O'Hare International Airport to Tampa
- Ave. Duration
- 2h 45m
- When
- Every day
- Estimated price
- $110–380
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Chicago Union Station to Tampa
- Ave. Duration
- 40h 47m
- Frequency
- Once daily
- Estimated price
- $950–1,600
- Website
- Amtrak
Train from Chicago Union Station to Milwaukee
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $45–75
- Website
- Amtrak
- Phone
- +1 888-968-7282
- Website
- Chicago Transit Authority
Subway from Adams/Wabash to Midway
- Ave. Duration
- 23 min
- Frequency
- Every 15 minutes
- Estimated price
- $2–5
- Website
- Chicago Transit Authority
- Schedules at
- Chicago Transit Authority Schedules & Routes
- Adult
- $2–5
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- Greyhound
Bus from Chicago Bus Station to Atlanta Bus Station
- Ave. Duration
- 16h 5m
- Frequency
- 4 times a day
- Estimated price
- $120–190
- Website
- Greyhound
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Chicago Bus Station to Atlanta Bus Station
- Ave. Duration
- 15h 40m
- Frequency
- Twice daily
- Estimated price
- $110–170
- Schedules at
- Flixbus USA
Bus from Atlanta Bus Station to Tampa Bus Station
- Ave. Duration
- 9h 10m
- Frequency
- 5 times a week
- Estimated price
- $80–130
- Schedules at
- Flixbus USA
- Phone
- +1 (941) 749-7116
- mcat@mymanatee.org
- Website
- mymanatee.org
Bus from Downtown Station to Psta Grand Central Station
- Ave. Duration
- 40 min
- Frequency
- Once daily
- Estimated price
- $1–8
- Schedules at
- mymanatee.org
- Seniors 80+, Children under 5
- $0
- Free trolleys
- $0
- students, Disabled, Seniors 60-79
- $1–8
- Adults 18-59
- $1–8
- Phone
- +1 727-540-1900
- ride@psta.net
- Website
- Pinellas Suncoast Transit Authority
Bus from Grand Central Station - C to Tyrone Square Mall Shelter - B
- Ave. Duration
- 20 min
- Frequency
- Every 30 minutes
- Estimated price
- $3
- Schedules at
- Pinellas Suncoast Transit Authority
- Adult
- $3
Bus from Tyrone Square Mall Shelter - C to Main St + Pine Tree Ln
- Ave. Duration
- 51 min
- Frequency
- Hourly
- Estimated price
- $3
- Schedules at
- Pinellas Suncoast Transit Authority
- Adult
- $3
Bus from Main St + Pine Tree Ln to Tampa Rd + Pinckney St
- Ave. Duration
- 22 min
- Frequency
- Hourly
- Estimated price
- $3
- Schedules at
- Pinellas Suncoast Transit Authority
- Adult
- $3
Want to know more about travelling around United States
Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.
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Booking & Getting There
Chicago to Oldsmar bus services, operated by Greyhound USA, arrive at Atlanta Bus Station.
Oldsmar is 1h ahead of Chicago. It is currently 5:41 PM in Chicago and 6:41 PM in Oldsmar.
Chicago to Oldsmar train services, operated by Amtrak, arrive at Tampa station.
Yes, the driving distance between Chicago to Oldsmar is 1126 miles. It takes approximately 20h 19m to drive from Chicago to Oldsmar.
There are 2338+ hotels available in Oldsmar.











