Dayton to Chicago is 1084 miles and takes about 20h 38m via Keystone Shortway, Ohio Turnpike, and I 84, with a fuel budget near $192 and enough daylight to finish in a day. This long-haul drive will take you from the Northeast region of Maine across to the Midwest. Given the 20+ hour duration, it's best planned as a 3-day trip. You'll be covering a significant amount of ground, so prepare for a substantial time commitment on the road.
Trip Pace
Best split across 3 days
Treat the return leg as its own travel day rather than an afterthought.
Break Rhythm
5 planned breaks
Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
Midpoint
542 miles from Dayton, ME
A natural place for your longest stop of the day
, about 10h 43m into the drive
.
Main Roads
Road
Distance
Duration
Keystone Shortway
272 mi
4h 54m
Ohio Turnpike
218.5 mi
3h 54m
I 84
197.7 mi
3h 56m
Indiana Toll Road
156.8 mi
2h 51m
I 495
54 mi
1h 2m
Maine Turnpike
44.3 mi
49m
American Legion Memorial Highway
35 mi
42m
Wilbur Cross Highway
33.6 mi
39m
Longest stretch:
Keystone Shortway
— 272 mi, about 4h 54m
Traffic on I-495
Hour-of-day weekday pattern from 173 FHWA count stations on your route.
Peak
3 PM
~3,985 veh/hr typical
· worst 4,640
Quietest
2 AM
~279 veh/hr
Peak-to-quiet ratio
14.3×
busier at peak than in the quiet hours
12a6anoon6p11p
Averaged across 52 weeks of 2023 FHWA Travel Monitoring Analysis System data. Weekday hours only (Mon–Fri).
Turn-by-Turn Driving Directions
Step-by-step road directions between Dayton, ME and Chicago, IL.
1
Start on Wilderness Drive
0.3 mi·1 min·Wilderness Drive
2
At end of road, turn left onto Bickford Road
0.4 mi·1 min·Bickford Road
3
Turn right onto Hollis Road
1.4 mi·5 min·Hollis Road
4
Turn left onto ME 5
4.6 mi·8 min·New County Road
5
Continue on ME 5
0.5 mi·58 sec·Bradley Street
6
Turn left onto Garfield Street
0.4 mi·1 min·Garfield Street
7
Turn right onto Shadagee Road
0.3 mi·1 min·Shadagee Road
8
At end of road, turn left onto ME 112
0.7 mi·1 min·North Street
9
Take the ramp
0.4 mi·52 sec
Toward I 95 South: Kittery, Portsmouth, NH
10
Merge onto I 95
44 mi·49 min·Maine Turnpike
Use the straight lane.
11
Keep slight left at fork onto I 95
7.7 mi·8 min·Blue Star Turnpike
Use the slight left / straight lanes.
12
Keep slight right at fork onto I 495
31 mi·35 min·I 495
Exit 89Toward I 495 South: WorcesterUse the straight / slight right lanes.
13
Take the exit
0.2 mi·14 sec
Exit 89C-B-AToward US 3: Burlington, Nashua New HampshireUse the straight / slight right lanes.
14
Keep slight left at fork
0.2 mi·17 sec
Toward US 3: Burlington, Nashua New Hampshire
15
Keep slight left at fork
0.4 mi·25 sec
16
Keep slight left at fork
0.5 mi·33 sec
Toward I 495 South: Marlboro
17
Merge onto I 495
23 mi·27 min·I 495
Use the straight / slight right lanes.
18
Take the exit
0.4 mi·1 min
Exit 65BToward I 290 West: Worcester
19
Merge onto I 290
20 mi·24 min·I 290
Use the straight / slight right lanes.
20
Take the exit
0.1 mi·22 sec
Exit 12BToward MA 12 South: Webster
21
Turn left onto Oxford Street
466 ft·10 sec·Oxford Street
22
At end of road, turn right onto MA 12
446 ft·9 sec·Southbridge Street
23
Take the exit
0.4 mi·1 min
Toward I 90
24
Keep slight left at fork
0.6 mi·1 min
Toward I 90 West
25
Merge onto I 90
11 mi·12 min·Massachusetts Turnpike
26
Keep slight right at fork onto I 84
34 mi·39 min·Wilbur Cross Highway
Exit 78Toward I 84: Hartford, New York CityUse the slight right lane.
27
Keep slight right at fork onto I 84
8.0 mi·9 min·I 84
Use the straight / right lanes.
28
Keep slight right at fork onto I 84; US 6
15 mi·19 min·I 84; US 6
Use the straight / slight left lanes.
29
Keep slight left at fork onto I 84
46 mi·55 min·I 84
Use the straight / slight right lanes.
30
Keep slight right at fork onto I 84
129 mi·2 hr 31 min·I 84
Use the straight / slight right lanes.
31
Take the exit
1.2 mi·2 min
Toward I 81 South: Wilkes-Barre
32
Merge onto I 81
35 mi·42 min·American Legion Memorial Highway
33
Take the exit
0.7 mi·1 min
Exit 151BToward I-80 West: Bloomsburg
34
Merge onto I 80
272 mi·4 hr 54 min·Keystone Shortway
35
Keep slight right at fork onto I 80
4.5 mi·5 min·I 80
36
Take the exit onto I 80
0.5 mi·1 min·I 80
Toward I 80 West, I 76 EastUse the slight right lane.
37
Keep slight right at fork onto I 80
0.4 mi·1 min·I 80
Toward I 80 West: Cleveland
38
Merge onto I 80
31 mi·33 min·Ohio Turnpike
39
Keep slight left at fork onto I 80
187 mi·3 hr 20 min·Ohio Turnpike
Use the straight / slight right lanes.
40
Continue on I 80; I 90
156 mi·2 hr 48 min·Indiana Toll Road
Use the straight / slight right lanes.
41
Turn straight onto I 90
0.2 mi·1 min·Indiana Toll Road
42
Merge onto I 90
1.0 mi·1 min·Indiana Toll Road
43
Continue on I 90
2.9 mi·5 min·Chicago Skyway
44
Turn straight onto I 90
0.1 mi·17 sec·Chicago Skyway
45
Merge onto I 90
4.1 mi·6 min·Chicago Skyway
Use the straight / slight right lanes.
46
Keep slight left at fork onto I 90
0.4 mi·30 sec·Chicago Skyway
Toward I 90 Express, I 94 ExpressUse the straight lane.
47
Merge onto I 90; I 94
5.5 mi·7 min·Dan Ryan Expressway (Express)
48
Take the exit
0.3 mi·39 sec
Exit 53AToward Canalport Avenue, Cermak RoadUse the straight / slight right lanes.
49
Turn slight left onto South Ruble Street
243 ft·6 sec·South Ruble Street
50
Turn slight left
75 ft·4 sec
51
Turn left onto South Canalport Avenue
0.2 mi·26 sec·South Canalport Avenue
52
Turn left onto South Halsted Street
0.1 mi·18 sec·South Halsted Street
53
Turn right onto West Cermak Road
0.2 mi·24 sec·West Cermak Road
54
Turn left
152 ft·11 sec
55
Turn right
0.2 mi·58 sec
56
Arrive at destination
Trip Plan
With a 20-hour drive time, you'll want to split this trip over 3 days to avoid fatigue. Consider leaving early in the morning on your first day to maximize daylight hours. Plan for around 5 stops, averaging about 7 hours of driving per day. Keep an eye on your fuel costs, budgeting around $192 for gas. Breaking up the drive with overnight stays is essential for safety and comfort.
Morning Departure
Start early — leave by 6-7 AM to arrive at a reasonable hour.
Evening Departure
This is a long drive — plan for a morning departure or consider splitting it into two days.
This drive is better paced as a 3-day trip.
Plan roughly 5 meaningful breaks for fuel, food, and rest.
The halfway point lands around 542 miles from Dayton, ME, or about 10h 43m into the drive.
The longest continuous stretch on this route runs about 272 miles.
Consider an overnight stop or starting very early.
Departure
Before you leave
Start with fuel, water, and navigation already sorted so the first hour feels easy.
First stop
Around 220 miles or 4h 32m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 542 miles or 10h 43m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Overnight split
Day 1 wrap after about 361.3 miles or 7h 20m
Stop before fatigue turns the last few hours into a grind. You want day two to start fresh, not just resumed.
Final approach
Final hour starts around 19h 24m
Traffic, exits, and arrival timing usually matter more near Chicago, IL than in the middle of the route.
Before You Leave
+
Open the route before leaving Dayton, ME so your first major turns are already loaded.
+
Leave with enough water and a charging cable within reach, not packed away.
+
Check your fuel range against the first long segment, especially if you are starting outside city service areas.
+
Pick one backup stop option before the midpoint in case traffic changes your pacing.
+
Treat this as a 3-day road trip and book the overnight stop before the busiest arrival window.
Day 1
Settle into the route from Dayton, ME
Aim for roughly 361 miles and 6.9 hours of wheel time on this day.
Day 2
Keep the middle miles efficient
Aim for roughly 361 miles and 6.9 hours of wheel time on this day.
Day 3
Finish the approach into Chicago, IL
Aim for roughly 361 miles and 6.9 hours of wheel time on this day.
Your first comfortable stop window is around 220 miles from Dayton, ME.
This route usually feels better as a 3-day drive than as one long push.
Plan about 5 real breaks rather than only quick fuel stops.
The longest stretch is on Keystone Shortway for about 272 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Place data sourced from public business listings. Hours and availability may vary.
Heads-up: tricky spots
5 of 46
5 decision points cluster between mile 61 and 1082.9 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
8
61 mi into trip|~1h 20m in|I 495
Keep slight right at fork onto I 495 toward I 495 South: Worcester
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight right lanes.
Exit 89
Toward I 495 South: Worcester
8
91.6 mi into trip|~1h 56m in
Take the exit toward US 3: Burlington, Nashua New Hampshire
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Exit 89C-B-A
Toward US 3: Burlington, Nashua New Hampshire
9
148.9 mi into trip|~3h 6m in|I 84 / Wilbur Cross Highway
Keep slight right at fork onto I 84 / Wilbur Cross Highway toward I 84: Hartford, New York City
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Exit 78
Toward I 84: Hartford, New York City
8
1077 mi into trip|~20h 27m in|I 90 / Chicago Skyway
Keep slight left at fork onto I 90 / Chicago Skyway toward I 90 Express, I 94 Express
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight lane.
Toward I 90 Express, I 94 Express
8
1082.9 mi into trip|~20h 35m in
Take the exit toward Canalport Avenue, Cermak Road
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Exit 53A
Toward Canalport Avenue, Cermak Road
Fuel & Cost
Regular Gas
$191.62 one way
$383.24 round trip
$4.49/gal25.4 MPG avg379 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.92
$209.89
$419.77
premium
$5.29
$225.72
$451.44
diesel
$5.35
$228.32
$456.65
Estimated Tolls: $32.41
Indiana Toll Road
(156.8 mi)$10.98
Ohio Turnpike
(218.5 mi)$10.92
Chicago Skyway
$6.15
Maine Turnpike
(44.3 mi)$2.66
Massachusetts Turnpike
(11.2 mi)$0.67
Blue Star Turnpike
(7.7 mi)$0.54
Chicago Skyway
(7 mi)$0.49
Toll estimates based on average 2024-2025 rates. EZ-Pass/SunPass discounts may lower the actual cost.
Estimated Trip Cost (one way, 1 person)
Fuel
$192
Tolls
$32
Hotel (2n)
$160–$280
Meals
$75–$150
Total
$459–$654
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 379.3 kg one way.
Prices: EIA weekly data, 2026-06-01.
Driving Electric?
About $114 in charging
· 4 stops
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
325.2
4
$113.82
$52.03
Efficient EV
271
3
$94.85
$43.36
EV Truck/SUV
433.6
5
$151.76
$69.38
Gas CO2
379 kg
EV CO2
127 kg (66% less)
This is a long EV road trip requiring 4 charging stops. Plan your route around charger locations and allow extra time for charging.
DC fast charging avg $0.35/kWh. Home charging avg $0.16/kWh. US grid CO2: 0.39 kg/kWh.
Travel Intel
Current conditions at both ends of the drive.
Forecast as of Jun 3, 2026
Origin
Dayton, ME
Afternoon
in Dayton on Wednesday
Local time
3:01 PM
EDT
Current temp
46°F
Partly Cloudy
NW 0 to 5 mph2% chanceLive forecast
Destination
Chicago, IL
Afternoon
in Chicago on Wednesday
Local time
2:01 PM
CDT
Current temp
56°F
Mostly Clear
ENE 0 to 15 mph0% chanceLive forecast
80°F
Columbus, PA
715 mi in
Seasonal Notes
Summer travel usually means heavier construction, hotter rest stops, and busier weekend traffic around major cities.
Winter travel shortens daylight, so a route that looks manageable on paper can feel much longer after dark.
Holiday weekends tend to make both departure and arrival windows slower than the raw route time suggests.
For long drives, weather on day two can matter just as much as conditions at departure, so check the whole travel window rather than only the first day.
Time zone
1 hour earlier
The destination clock does not match departure time, so double-check hotel check-in windows and late arrival plans.
Temperature spread
10 degrees warmer at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
20h 38m on the road
This is long enough that the arrival forecast matters almost as much as departure conditions. Recheck both ends before you roll.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
More Details
What kind of drive is this?
This trip is a long-haul drive, with 52% of the route on highways. You'll experience a significant stretch of 272 miles on the Keystone Shortway. Expect a good amount of highway cruising, interspersed with periods where you'll transition to surface roads. The density of exits on the turnpike sections will be noticeable.
52% highway, the rest on surface roads — varied driving throughout.
56 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 272 mi on Keystone Shortway.
How Hard Is This Drive?
10/10
At 20h 38m, this is a long-haul route where pacing matters more than any single turn. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 61 miles in near I 495.
Driving Effort10/10
High effort - long or complex enough to need steady focus all day
Balances navigation complexity with total wheel time.
This is a demanding drive. With 46 significant decision points across 1084 miles, you will need to stay alert - especially through interchange areas and urban stretches. Consider splitting it into segments if you are not comfortable with fast highway navigation.
Where does it get tricky?
The main spots that need attention: at 61 miles (I 495): Highway fork - watch signs carefully. Lane positioning matters here; at 91.6 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 148.9 miles (I 84 / Wilbur Cross Highway): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Elevation Profile
Gently rolling terrain
1,571 ft49 ft
Total Climb
2,517 ft
Total Descent
2,128 ft
Highest Point
1,571 ft
~542 mi in
Elevation Range
1,522 ft
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Dayton, ME and Chicago, IL, road signs point toward Nashua New Hampshire and New York City.
Chicago is the home of the blues and the truth of jazz, the heart of comedy and the idea of the skyscraper. Here, the age of railroads found its center, and airplanes followed suit. "Stormy, Husky, Brawling / City of Big Shoulders," Chicago is a Heartland boomtown, its ethos defined by urban planner Daniel Burnham's immortal vision: "Make no little plans; they have no magic to stir men's blood." It is one of the world's great cities and the third largest city in the United States, behind only New York City and Los Angeles.
As the hub of the Midwest, Chicago is easy to find — its picturesque skyline calls across the waters of Lake Michigan, a first impression that soon reveals world-class museums of art and science, miles of sandy beaches, huge parks and public art, and perhaps the finest downtown collection of modern architecture in the world.
Top landmarks
•Willis Tower — skyscraper in Chicago, Illinois
•Art Institute of Chicago — art museum and school in Chicago, United States
•Wrigley Field — baseball stadium in Chicago, Illinois, USA; home venue of the Chicago Cubs
The longest stretch is about 272 miles on Keystone Shortway. The full list of main roads is in the Roads section above.
Yes — a 3-day pace is more comfortable than one long haul. A sensible stopping point is after roughly 361 miles on day one.
Expect about $32.41 in tolls one way, starting with Indiana Toll Road. Most Northeast and Midwest toll agencies accept E-ZPass; in the West and Texas, transponders like TxTag or FasTrak apply. If you do not have a transponder, cashless tolling plates will mail a bill to the vehicle's registered address — usually with a surcharge, so a rental-car toll pass is often cheaper than paying by mail.
Yes — we found about 130 rest areas or service plazas within a short detour of the route (from OpenStreetMap). See the Rest Stops tab under Nearby Places for locations and mile markers. Plan to stretch, use the bathroom, and top off fluids every 2–3 hours on longer drives.
It helps. This route has a higher-than-average number of complex decision points, which get harder in the dark. If the last hour of the trip is on surface roads or mountain grades, aim to arrive at Chicago, IL before sunset when you can. Check the Trip Plan for departure windows that land you in daylight.
Only with planning. This is a long drive for kids — consider splitting it into two days rather than pushing through. Plan at least 5 meaningful breaks. There are 130 rest areas along the route for bathroom stops.
Mostly yes along the main roads, but rural stretches through ME can have sparse or no coverage. Before you leave, download offline Google Maps or Apple Maps for the route, and consider downloading music or podcasts instead of streaming. If you depend on data for navigation, keep a paper backup of the turn-by-turn directions.
The main spots that need attention: at 61 miles (I 495): Highway fork - watch signs carefully. Lane positioning matters here; at 91.6 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 148.9 miles (I 84 / Wilbur Cross Highway): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Not recommended in a single day. At 20.6 hours each way, a round trip means 41.3 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Chicago, IL before the return drive.
