The cheapest and fastest trains from Bridgeport, CT to Chicago, IL
Cheapest price
$433
Average price
$1151
Fastest journey
22 h 50 m
Average duration
1 d 1 h 45 m
Trains per day
3
Distance
1204 km
The best way to find a cheap train ticket from Bridgeport, CT to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Bridgeport, CT to Chicago, IL will cost around $1151 if you buy it on the day, but the cheapest tickets can be found for only $433.
It's difficult to get from Bridgeport, CT to Chicago, IL without transferring at least once.
141 Northeast Regional · 43 Pennsylvanian · 40 Floridian
141 Northeast Regional · 40 Floridian
93 Northeast Regional · 49 Lake Shore Limited
93 Northeast Regional · 49 Lake Shore Limited
141 Northeast Regional · 43 Pennsylvanian · 40 Floridian
141 Northeast Regional · 40 FloridianTravel Information
Compare train, bus, and flight for Bridgeport, CT to Chicago, IL
Omio recommends booking the train as it is the most popular option from Bridgeport, CT to Chicago, IL among Omio's users. If you are prioritising price take the flight with prices starting from €96. For those with little time consider booking a flight which can get you there in 3h 3m. The ticket price range depends on the travel mode: a flight costs an average of €96, and a train costs an average of €211.
Distance: 748 miles (1204 km)
Compare train with
Most popular Train | Flight | Bus |
|---|---|---|
€294 Average price | €139 Average price Cheapest | €200 Average price |
25h 47m Average total duration 25h 17m Onboard + 30m Additional time* | 6h 3m Average total duration Fastest 3h 3m Onboard + 3h 0m Additional time* | 25h 15m Average total duration 24h 45m Onboard + 30m Additional time* |
![]() Most popular train company | ![]() Most popular airline | ![]() Most popular bus company |
Direct Options | Direct Options | Direct Options |
Live departures
Bridgeport, CT to Chicago, IL train times
The table below shows live departures for Bridgeport, CT to Chicago, IL trains for tomorrow, Friday, November 7. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
141 Northeast Regional · 40 Floridian | 11:32 AM Bridgeport Station, Bridgeport, CT | 27h13 | 2:45 PM Chicago Union Station, Chicago, IL | 1 transfer | |
141 Northeast Regional · 43 Pennsylvanian · 40 Floridian | 11:32 AM Bridgeport Station, Bridgeport, CT | 27h13 | 2:45 PM Chicago Union Station, Chicago, IL | 2 transfers | |
93 Northeast Regional · 49 Lake Shore Limited | 5:22 PM Bridgeport Station, Bridgeport, CT | 22h50 | 4:12 PM Chicago Union Station, Chicago, IL | 1 transfer | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets Bridgeport, CT to Chicago, IL by train, bus, or flight
Compare train, bus, and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Nov 07
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Journey information
Overview: Train from Bridgeport, CT to Chicago, IL
Trains from Bridgeport, CT to Chicago, IL run on average 3 times per day, taking around 25h 17m. Cheap train tickets for this journey start at $259 (€211) but you can travel from only $118 (€96) by flight.
The earliest train runs at 07:56, the last at 18:40. The fastest train covers the 748 miles (1204 km) distance in 22h 44m.
Distance 748 miles (1204 km) |
Average train duration 25h 17m |
Cheapest ticket price $259 (€211) |
Trains per day 3 |
Fastest train 22h 44m |
First train 07:56 |
Last train 18:40 |
Train companies: Amtrak, Metro-North Railroad (MNR) from Bridgeport, CT to Chicago, IL trainsAmtrak, Metro-North Railroad (MNR) trains will get you between Bridgeport, CT and Chicago, IL from $118 (€96). With over 1000 travel companies on Omio, you can find the best train times and tickets for your trip.
Amtrak
Metro-North Railroad (MNR)
FAQs: Trains from Bridgeport, CT to Chicago, IL
Find answers to the most common questions about traveling from Bridgeport, CT to Chicago, IL by train. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest train, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

popular train stations
Popular train stations from Bridgeport, CT to Chicago, IL
- 5:00 AM - 10:00 PM Monday - Sunday
- Free
- Parking is available 7 days a week with access from Water Street.
- Ralph 'n' Rich's
- Boca Oyster Bar
- Outside the main entrance.
- Ramps, restrooms.
- $0.50
- Holiday Inn Bridgeport-Trumbull-Fairfield
- Hampton Inn by Hilton Shelton
- Quality Suites
- Located in the main hall
- Located in the main hall
- Free
- The station has a main concourse with access to platforms and ticketing services.
- Bus: Greater Bridgeport Transit (GBT) buses available
- Ferry: Bridgeport & Port Jefferson Ferry nearby
- 5:00 AM - 12:00 AM Monday - Sunday
- Free
- The car park is open 7 days a week from 5:00 a.m. to 12:00 a.m. Departures can be made outside of opening hours. Access via Canal Street.
- The Chicago Firehouse Restaurant
- Lou Mitchell's
- Outside the main entrance.
- Elevators, ramps, restrooms.
- $1
- The Kimpton Gray Hotel
- JW Marriott Chicago
- W Chicago - City Center
- Located in the main hall
- Located in the main hall
- Avis
- Budget
- Enterprise
- Located in the main hall
- Free
- Hall 1: main entrance, Amtrak services
- Hall 2: Metra services
- Hall 3: food court and retail shops
- Bus: Several lines available
- CTA: Blue Line, Pink Line
Most popular train connections from Bridgeport, CT
More options for your journey from Bridgeport, CT to Chicago, IL
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