There are 8 ways to get from Chicago to Diamondhead by plane, train, taxi, bus (Flixbus, Greyhound), car, or bus (Greyhound)
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 Gulfport-Biloxi Regional Airport
best- Fly from Chicago O'Hare International Airport (ORD) to Gulfport-Biloxi Regional Airport (GPT)plane ORD - GPT
6h 36m$148–565Train, taxi (Amtrak)
- Take the train from Chicago Union Station to New Orleans Union Passenger Terminaltrain
- Take the train from New Orleans Union Passenger Terminal to Picayune Amtrak Stationtrain
- Take the taxi from Picayune Amtrak Station to Diamondheadtaxi
22h 45m$336–670Bus via Newnan
- Take the bus from Chicago Bus Station to Atlanta Bus Stationbus
- Take the bus from Washington St at MLK Jr Dr to Newnan Park and Ridebus 453
- Take the bus from Newnan Park and Ride to Gulfportbus
23h 13m$222–406Drive 900.3 mi
- Drive from Chicago to Diamondheadcar 900.3 mi
15h 8m$165–238Fly Chicago Midway International Airport to Gulfport-Biloxi Regional Airport
- Fly from Chicago Midway International Airport (MDW) to Gulfport-Biloxi Regional Airport (GPT)plane MDW - GPT
6h 10m$188–775Fly Chicago Midway International Airport to Louis Armstrong New Orleans International Airport, train, taxi
- Fly from Chicago Midway International Airport (MDW) to Louis Armstrong New Orleans International Airport (MSY)plane MDW - MSY
- Take the train from New Orleans Union Passenger Terminal to Picayune Amtrak Stationtrain
- Take the taxi from Picayune Amtrak Station to Diamondheadtaxi
8h 14m$174–604Fly Chicago O'Hare International Airport to Louis Armstrong New Orleans International Airport, train, taxi
- Fly from Chicago O'Hare International Airport (ORD) to Louis Armstrong New Orleans International Airport (MSY)plane ORD - MSY
- Take the train from New Orleans Union Passenger Terminal to Picayune Amtrak Stationtrain
- Take the taxi from Picayune Amtrak Station to Diamondheadtaxi
8h 41m$168–464Bus (Greyhound)
- Take the bus from Chicago Train Station to Atlanta Bus Stationbus Greyhound US0100
- Take the bus from Atlanta Bus Station to Biloxi Transit Centerbus Greyhound US0602
28h 30m$258–443
Chicago O'Hare International Airport (ORD) to Gulfport-Biloxi Regional Airport (GPT) flights
Questions & Answers
The cheapest way to get from Chicago to Diamondhead is to drive which costs $160 - $240 and takes 15h 8m.
The fastest way to get from Chicago to Diamondhead is to fly which takes 6h 10m and costs $180 - $800.
The distance between Chicago and Diamondhead is 846 miles. The road distance is 905.5 miles.
The best way to get from Chicago to Diamondhead without a car is to train and taxi which takes 22h 45m and costs $330 - $700.
It takes approximately 6h 36m to get from Chicago to Diamondhead, including transfers.
The best way to get from Chicago to Diamondhead is to fly which takes 6h 36m and costs $140 - $600. Alternatively, you can bus via Newnan, which costs $220 - $410 and takes 23h 13m.
Yes, the driving distance between Chicago to Diamondhead is 906 miles. It takes approximately 15h 8m to drive from Chicago to Diamondhead.
There are 634+ hotels available in Diamondhead.
What companies run services between Chicago, IL, USA and Diamondhead, MS, USA?
Delta, American Airlines, and United Airlines fly from Chicago O'Hare International Airport (ORD) to Gulfport-Biloxi Regional Airport (GPT) every 3 hours. Alternatively, you can take a bus from Chicago Bus Station to Diamondhead via Atlanta Bus Station, Washington St at MLK Jr Dr, Newnan Park and Ride, and Gulfport in around 23h 13m.
- Website
- southwest.com
Flights from Chicago Midway International Airport to Louis Armstrong New Orleans International Airport
- Ave. Duration
- 2h 22m
- When
- Every day
- Estimated price
- $85–470
Flights from Chicago Midway International Airport to Louis Armstrong New Orleans International Airport via Kansas City
- Ave. Duration
- 4h 15m
- When
- Tuesday, Wednesday, and Sunday
- Estimated price
- $100–550
Flights from Chicago Midway International Airport to Louis Armstrong New Orleans International Airport via Nashville
- Ave. Duration
- 4h 33m
- When
- Tuesday and Wednesday
- Estimated price
- $90–480
Flights from Chicago O'Hare International Airport to Louis Armstrong New Orleans International Airport via Nashville
- Ave. Duration
- 4h 40m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $60–330
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Gulfport-Biloxi Regional Airport via Charlotte
- Ave. Duration
- 6h 11m
- When
- Every day
- Estimated price
- $100–550
Flights from Chicago O'Hare International Airport to Gulfport-Biloxi Regional Airport via Dallas/Ft.Worth
- Ave. Duration
- 5h 56m
- When
- Every day
- Estimated price
- $110–600
Flights from Chicago Midway International Airport to Gulfport-Biloxi Regional Airport via Charlotte
- Ave. Duration
- 5h 11m
- When
- Tuesday, Saturday, and Sunday
- Estimated price
- $150–800
Flights from Chicago O'Hare International Airport to Louis Armstrong New Orleans International Airport
- Ave. Duration
- 2h 29m
- When
- Every day
- Estimated price
- $60–330
- Website
- delta.com
Flights from Chicago O'Hare International Airport to Gulfport-Biloxi Regional Airport via Atlanta
- Ave. Duration
- 6h 1m
- When
- Every day
- Estimated price
- $90–490
Flights from Chicago Midway International Airport to Gulfport-Biloxi Regional Airport via Atlanta
- Ave. Duration
- 5h 21m
- When
- Every day
- Estimated price
- $130–700
Flights from Chicago Midway International Airport to Louis Armstrong New Orleans International Airport via Atlanta
- Ave. Duration
- 4h 33m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $100–550
- Website
- united.com
Flights from Chicago O'Hare International Airport to Gulfport-Biloxi Regional Airport via Houston
- Ave. Duration
- 5h 45m
- When
- Every day
- Estimated price
- $110–600
Flights from Chicago O'Hare International Airport to Louis Armstrong New Orleans International Airport
- Ave. Duration
- 2h 38m
- When
- Every day
- Estimated price
- $60–330
- Website
- spirit.com
Flights from Chicago O'Hare International Airport to Louis Armstrong New Orleans International Airport
- Ave. Duration
- 2h 25m
- When
- Every day
- Estimated price
- $80–270
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Chicago Union Station to New Orleans Union Passenger Terminal
- Ave. Duration
- 19h 42m
- Frequency
- Once daily
- Estimated price
- $250–550
- Website
- https://www.amtrak.com/home.html
Train from New Orleans Union Passenger Terminal to Picayune Amtrak Station
- Ave. Duration
- 1h 20m
- Frequency
- Once daily
- Estimated price
- $14–35
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 (855) 626-8585
- Website
- flixbus.com
Bus from Chicago Bus Station to Atlanta Bus Station
- Ave. Duration
- 14h 25m
- Frequency
- 3 times a day
- Estimated price
- $85–160
- Schedules at
- flixbus.com
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- greyhound.com
Bus from Chicago Bus Station to Atlanta Bus Station
- Ave. Duration
- 16h 25m
- Frequency
- 4 times a day
- Estimated price
- $120–240
- Website
- https://www.greyhound.com/
Bus from Chicago Train Station to Atlanta Bus Station
- Ave. Duration
- 16h 5m
- Frequency
- Twice daily
- Estimated price
- $120–240
- Website
- https://www.greyhound.com/
Bus from Atlanta Bus Station to Biloxi Transit Center
- Ave. Duration
- 9h 5m
- Frequency
- Twice daily
- Estimated price
- $75–140
- Website
- https://www.greyhound.com/
- Phone
- +1 844-977-7742
- Website
- xpressga.com
Bus from Washington St at MLK Jr Dr to Newnan Park and Ride
- Ave. Duration
- 51 min
- Frequency
- 3 times a day
- Estimated price
- $3–4
- Website
- https://xpressga.com
- Phone
- +1 800-923-1799
- contactus@omexusa.net
- Website
- omnibusexpress.com
Bus from Newnan Park and Ride to Gulfport
- Ave. Duration
- 5h 12m
- Frequency
- Once daily
- Estimated price
- $75–100
- Schedules at
- omnibusexpress.com
- Ave. Duration
- 43 min
- Estimated price
- $70–90
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