There are 11 ways to get from Chicago to Oxford by plane, bus (Flixbus, Greyhound), train (Amtrak), car, bus, 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 Chicago O'Hare International Airport to Tweed-New Haven Airport
best- Fly from Chicago O'Hare International Airport (ORD) to Tweed-New Haven Airport (HVN)plane ORD - HVN
4h 49m$228–560Fly Chicago O'Hare International Airport to Bradley International Airport, bus
cheapest- Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane ORD - BDL
- Take the bus from Main St @ Atheneum Sq to E Main St @ Phoenix Stbus
6h 57m$90–428Bus
- Take the bus from Chicago Bus Station to New York Midtownbus FlixBus N2641 / ...
- Take the bus from Port Authority Bus Terminal to New Haven Union Stationbus New York
20h 35m$199–334Train (Amtrak)
- Take the train from Chicago Union Station to Springfieldtrain Lake Shore Limited
- Take the train from Springfield to New Haventrain Amtrak Hartford Line / ...
21h 58m$357–706Drive 855.9 mi
- Drive from Chicago to Oxfordcar 855.9 mi
14h 16m$157–226Fly Chicago Midway International Airport to Bradley International Airport, bus
- Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane MDW - BDL
- Take the bus from Main St @ Atheneum Sq to E Main St @ Phoenix Stbus
6h 26m$116–528Fly Chicago Midway International Airport to Laguardia Airport, train
- Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane MDW - LGA
- Take the train from 125th Street - Harlem to Bridgeporttrain
7h 48m$240–613Fly Chicago O'Hare International Airport to Laguardia Airport, train
- Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane ORD - LGA
- Take the train from 125th Street - Harlem to Bridgeporttrain
8h 8m$250–713Fly Chicago O'Hare International Airport to Westchester County Airport, line 971 bus, train
- Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane ORD - HPN
- Take the bus from Main St @ South Broadway to Stamford Transportation Center @ Bay Abus
- Take the train from Stamford to Bridgeporttrain
- Take the train from Bridgeport to Seymourtrain
9h 20m$128–554Train via New York (Amtrak)
- Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain Lake Shore Limited / ...
- Take the train from Ny Moynihan Train Hall At Penn Station to Bridgeport Amtrak Stationtrain Northeast Regional / ...
24h 29m$344–695Bus, train
- Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus
- Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus
- Take the train from Grand Central Terminal to Bridgeporttrain
25h 42m$197–405
Chicago O'Hare International Airport (ORD) to Tweed-New Haven Airport (HVN) flights
Questions & Answers
The cheapest way to get from Chicago to Oxford is to drive which costs $150 - $230 and takes 14h 16m.
The fastest way to get from Chicago to Oxford is to fly which takes 4h 49m and costs $220 - $600.
No, there is no direct bus from Chicago station to Oxford station. However, there are services departing from Chicago Bus Station and arriving at New Haven Union Station via Port Authority Bus Terminal. The journey, including transfers, takes approximately 20h 35m.
No, there is no direct train from Chicago station to Oxford. However, there are services departing from Chicago Union Station and arriving at New Haven via Springfield. The journey, including transfers, takes approximately 21h 58m.
The distance between Chicago and Oxford is 817 miles. The road distance is 860.9 miles.
The best way to get from Chicago to Oxford without a car is to bus which takes 20h 35m and costs $190 - $340.
It takes approximately 4h 49m to get from Chicago to Oxford, including transfers.
Chicago to Oxford bus services, operated by Flixbus USA, depart from Chicago Bus Station.
Chicago to Oxford train services, operated by Amtrak, depart from Chicago Union Station.
The best way to get from Chicago to Oxford is to fly which takes 4h 49m and costs $220 - $600. Alternatively, you can bus, which costs $190 - $340 and takes 20h 35m, you could also train, which costs $350 - $750 and takes 21h 58m.
What companies run services between Chicago, IL, USA and Oxford, CT, USA?
Avelo Airlines flies from Chicago O'Hare International Airport (ORD) to Tweed-New Haven Airport (HVN) 4 times a week. Alternatively, you can take a bus from Chicago Bus Station to Oxford via New York Midtown, Port Authority Bus Terminal, and New Haven Union Station in around 20h 35m.
- Website
- southwest.com
Flights from Chicago Midway International Airport to Bradley International Airport
- Ave. Duration
- 2h 7m
- When
- Every day
- Estimated price
- $100–500
Flights from Chicago Midway International Airport to Bradley International Airport via Baltimore
- Ave. Duration
- 4h 29m
- When
- Every day
- Estimated price
- $110–550
Flights from Chicago Midway International Airport to Laguardia Airport
- Ave. Duration
- 2h 4m
- When
- Every day
- Estimated price
- $120–650
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Bradley International Airport
- Ave. Duration
- 2h 24m
- When
- Every day
- Estimated price
- $75–400
Flights from Chicago O'Hare International Airport to Bradley International Airport via Reagan Washington
- Ave. Duration
- 4h 41m
- When
- Every day
- Estimated price
- $85–430
Flights from Chicago O'Hare International Airport to Laguardia Airport
- Ave. Duration
- 2h 16m
- When
- Every day
- Estimated price
- $100–550
Flights from Chicago O'Hare International Airport to Westchester County Airport
- Ave. Duration
- 2h 19m
- When
- Every day
- Estimated price
- $95–500
Flights from Chicago O'Hare International Airport to Westchester County Airport via Reagan Washington
- Ave. Duration
- 4h 34m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $100–550
Flights from Chicago O'Hare International Airport to Westchester County Airport via Charlotte
- Ave. Duration
- 5h 23m
- When
- Every day
- Estimated price
- $130–650
- Website
- united.com
Flights from Chicago O'Hare International Airport to Bradley International Airport
- Ave. Duration
- 2h 22m
- When
- Every day
- Estimated price
- $75–400
Flights from Chicago O'Hare International Airport to Bradley International Airport via Washington Dulles
- Ave. Duration
- 4h 54m
- When
- Every day
- Estimated price
- $85–420
Flights from Chicago O'Hare International Airport to Laguardia Airport
- Ave. Duration
- 2h 22m
- When
- Every day
- Estimated price
- $100–550
- Website
- delta.com
Flights from Chicago Midway International Airport to Bradley International Airport via Detroit
- Ave. Duration
- 4h 9m
- When
- Every day
- Estimated price
- $100–500
Flights from Chicago O'Hare International Airport to Bradley International Airport via Detroit
- Ave. Duration
- 4h 51m
- When
- Every day
- Estimated price
- $75–400
Flights from Chicago Midway International Airport to Laguardia Airport via Detroit
- Ave. Duration
- 4h
- When
- Every day
- Estimated price
- $130–700
Flights from Chicago O'Hare International Airport to Laguardia Airport
- Ave. Duration
- 2h 23m
- When
- Every day
- Estimated price
- $100–550
Flights from Chicago O'Hare International Airport to Westchester County Airport via Detroit
- Ave. Duration
- 4h 5m
- When
- Every day
- Estimated price
- $95–500
- Website
- aveloair.com
Flights from Chicago O'Hare International Airport to Tweed-New Haven Airport
- Ave. Duration
- 2h 32m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $140–450
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Chicago Union Station to Springfield
- Ave. Duration
- 19h 19m
- Frequency
- Once daily
- Estimated price
- $290–600
- Website
- https://www.amtrak.com/home.html
Train from Springfield to New Haven
- Ave. Duration
- 1h 15m
- Frequency
- Every 4 hours
- Estimated price
- $19–45
- Website
- https://www.amtrak.com/home.html
Train from Stamford to Bridgeport
- Ave. Duration
- 30 min
- Frequency
- Every 2 hours
- Estimated price
- $7–15
- Website
- https://www.amtrak.com/home.html
Train from Chicago Union Station to Ny Moynihan Train Hall At Penn Station
- Ave. Duration
- 20h 12m
- Frequency
- Once daily
- Estimated price
- $300–650
- Website
- https://www.amtrak.com/home.html
Train from Ny Moynihan Train Hall At Penn Station to Bridgeport Amtrak Station
- Ave. Duration
- 1h 20m
- Frequency
- Hourly
- Estimated price
- $18–40
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 877.690.5114
- Website
- mta.info
Train from 125th Street - Harlem to Bridgeport
- Ave. Duration
- 1h 21m
- Frequency
- Every 30 minutes
- Estimated price
- $15–23
- Website
- https://www.mta.info/agency/metro-north-railroad
- Schedules at
- https://www.mta.info/schedules
- Off-Peak
- $15–17
- Peak
- $20–23
Train from 125th Street - Harlem to Bridgeport
- Ave. Duration
- 1h 21m
- Frequency
- Every 30 minutes
- Estimated price
- $15–23
- Website
- https://www.mta.info/agency/metro-north-railroad
- Schedules at
- https://www.mta.info/schedules
- Off-Peak
- $15–17
- Peak
- $20–23
Train from Stamford to Bridgeport
- Ave. Duration
- 42 min
- Frequency
- Every 30 minutes
- Estimated price
- $9–15
- Website
- https://www.mta.info/agency/metro-north-railroad
- Schedules at
- https://www.mta.info/schedules
- Off-Peak
- $9–11
- Peak
- $13–15
Train from Bridgeport to Seymour
- Ave. Duration
- 42 min
- Frequency
- Every 3 hours
- Estimated price
- $8–14
- Website
- https://www.mta.info/agency/metro-north-railroad
- Schedules at
- https://www.mta.info/schedules
- Off-Peak
- $8–10
- Peak
- $12–14
Train from Grand Central Terminal to Bridgeport
- Ave. Duration
- 1h 31m
- Frequency
- Every 30 minutes
- Estimated price
- $15–24
- Website
- https://www.mta.info/agency/metro-north-railroad
- Schedules at
- https://www.mta.info/schedules
- Off-Peak
- $15–18
- Peak
- $22–24
- Phone
- +1 (855) 626-8585
- Website
- https://www.flixbus.com
Bus from Chicago Bus Station to New York Midtown
- Ave. Duration
- 17h 5m
- Frequency
- Twice daily
- Estimated price
- $140–240
- Schedules at
- flixbus.com
- Phone
- 1-800-343-9999
- Website
- peterpanbus.com
Bus from Port Authority Bus Terminal to New Haven Union Station
- Ave. Duration
- 1h 55m
- Frequency
- Every 4 hours
- Estimated price
- $16–40
- Website
- https://peterpanbus.com
Bus from Baltimore Downtown Bus Station to Port Authority Bus Terminal
- Ave. Duration
- 3h 44m
- Frequency
- Every 2 hours
- Estimated price
- $45–130
- Website
- https://peterpanbus.com
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- greyhound.com
Bus from Port Authority Bus Terminal to New Haven Union Station
- Ave. Duration
- 2h 5m
- Frequency
- Every 4 hours
- Estimated price
- $11–22
- Website
- https://www.greyhound.com/
Bus from Chicago Bus Station to Baltimore Downtown Bus Station
- Ave. Duration
- 17h 45m
- Frequency
- Twice daily
- Estimated price
- $110–220
- Website
- https://www.greyhound.com/
Bus from Baltimore Downtown Bus Station to Port Authority Bus Terminal
- Ave. Duration
- 3h 20m
- Frequency
- Every 3 hours
- Estimated price
- $35–70
- Website
- https://www.greyhound.com/
- Phone
- +1 860-525-9181
- Website
- cttransit.com
Bus from Main St @ Atheneum Sq to E Main St @ Phoenix St
- Ave. Duration
- 1h 5m
- Frequency
- Hourly
- Estimated price
- $2–6
- Website
- https://www.cttransit.com
- Book at
- https://buypasses.storesecured.com
- Two-Hour Pass
- $2
- Two-Hour Pass express
- $4–6
Bus from Main St @ Atheneum Sq to E Main St @ Phoenix St
- Ave. Duration
- 1h 5m
- Frequency
- Hourly
- Estimated price
- $2–6
- Website
- https://www.cttransit.com
- Book at
- https://buypasses.storesecured.com
- Two-Hour Pass
- $2
- Two-Hour Pass express
- $4–6
Bus from Main St @ South Broadway to Stamford Transportation Center @ Bay A
- Ave. Duration
- 25 min
- Frequency
- Hourly
- Estimated price
- $2–4
- Website
- https://www.cttransit.com
- Book at
- https://buypasses.storesecured.com
- Two-Hour Pass
- $2
- Two-Hour Pass express
- $3–4
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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More Questions & Answers
Chicago to Oxford bus services, operated by Flixbus USA, arrive at New York Midtown station.
Oxford is 1h ahead of Chicago. It is currently 6:35 AM in Chicago and 7:35 AM in Oxford.
Chicago to Oxford train services, operated by Amtrak, arrive at Springfield station.
Yes, the driving distance between Chicago to Oxford is 861 miles. It takes approximately 14h 16m to drive from Chicago to Oxford.
There are 220+ hotels available in Oxford.












