Winona, MN → Chicago, IL
252 mi · 5h 2m (driving)
Current Risk
Low Risk
Clear conditions along your route
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Winona
29°
Town of Ithaca
37°
Town of La Prairie
37°
Chicago
37°
Wind gusts up to 21 mph — allow extra time
Trip Briefing
3 segments · 252 mi · 5h 3m
Weather
⛅ Partly cloudy
37°F, wind 11 mph
Rest Stops
13
Restrooms, Truck svc
Cameras
5 live
Clear driving conditions expected
Rest stops in this segment:
- ● Nodine Truck Stop
- ● Dresbach Rest Area 🚻
- ● La Crosse Rest Area 31 🚻
Hazards Ahead
3 road closures may affect your route · 47 construction zones on route
47 Construction Zones on Route
WI-21 eastbound: Roadwork - Mainline Flagging Operation on WIS 21 EB from County B to N Rusk Ave. Daily from 11/09/2026 to 11/13/2026, 07:00 AM - 05:00 PM, M, T, W, Th, F
WI-16 eastbound: Roadwork - Mainline Flagging Operation on WIS 16 EB from Hollister Ave to US 12 WB (End Divided). Daily from 11/09/2026 to 11/13/2026, 07:00 AM - 05:00 PM, M, T, W, Th, F
WI-16 eastbound: Roadwork - Mainline Right Lane Closed on WIS 16 EB from US 12 EB (Begin CC) to Sime Ave. Daily from 11/09/2026 to 12/11/2026, 07:00 AM - 04:00 PM, M, T, W, Th, F (excluding Sun, Sat)
US-12 eastbound: Roadwork - Mainline Flagging Operation on US 12 EB from Grain Ave to Monroe - Juneau CO Line. Daily from 08/26/2026 to 11/30/2026, 06:30 AM - 06:30 PM, M, T, W, Th, F (excluding Sun, Sat)
WI-16 eastbound: Roadwork - Mainline Flagging Operation on WIS 16 EB from Monroe - Juneau CO Line to Leer St. Daily from 08/26/2026 to 11/30/2026, 06:30 AM - 06:30 PM, M, T, W, Th, F (excluding Sun, Sat)
I-90 eastbound: Roadwork - Mainline Left Shoulder Closed at H (Bridge Crossing). Daily from 11/13/2026 to 11/13/2026, 06:00 AM - 12:00 PM, F
+ 41 more zones along the route — see map for full list
Highway Message Signs
US 12/18 US 12/18 EB @ E of West Broadway (MM 264.2)
FLEX LANE | CLOSED TO TRAFFIC | SILVER ALERT | WHITE HONDA SUV | WI LIC: AZJ2923
US 12/18 US 12/18 WB @ W of Stoughton Rd (MM 265.6)
FLEX LANE | CLOSED TO TRAFFIC | SILVER ALERT | WHITE HONDA SUV | WI LIC: AZJ2923
US 12/18 US 12/18 WB @ Agriculture/Marsh Dr
FLEX LANE | CLOSED TO TRAFFIC | SILVER ALERT | WHITE HONDA SUV | WI LIC: AZJ2923
Traffic Cameras
See recent road conditions along your route
Images are snapshots updated periodically by state DOTs. Timestamps shown in images indicate when each photo was captured.
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Selected Route
Via US-14 East → US-61 South → ... → I-94 West (John F. Kennedy Expressway) → Eisenhower Expressway
Cameras shown are along this computed route
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U.S.61 SB @ I-90
MN · SB
I-90 EB (La Crescent - MP 276.4) View 5
MN · EB
I-90 at County B (French Island)
La Crosse, WI ·
I-90 at WIS 131
Monroe, WI ·
I-90/94 at County PP
Monroe, WI ·
I-90/94 at County HH
Juneau, WI ·
I-90/94 at County T
Sauk, WI ·
I-90 EB: Randall Rd at I-90EB
IL · EB
I-90 EB: I-90/I190 Merge HD
IL · EB
I-39/90/94 at County V
Dane, WI ·
I-39/90 at County B
Dane, WI ·
I-39/90 at County S
Rock, WI ·
Live traffic on this route
Cameras, crashes and closures right now on the highways this drive uses.
Rest Stops Along Your Route
53 stops available
Swipe to see moreShowing 1-2 of 53
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We'll notify you when conditions change before your trip. Never drive into a surprise storm again.
⚡ Recent Weather Events on This Route
Premium users received alerts for these conditions:
- 🌧️Nov 11: Rain advisory for afternoon departures
- ❄️Nov 9: Snow expected at higher elevations - consider earlier departure
- 🌫️Nov 6: Dense fog warning for morning travel
Don't miss the next alert →
Driving from Winona, MN to Chicago, IL covers 252 miles in roughly 5h 2m of drive time, crossing state lines. We track 12 live traffic cameras, 53 rest areas and 3 reported incidents along this corridor so you can plan around them. Most drivers do this trip in one day; weather along the route matters more than the forecast at either endpoint, since you'll cross several climate zones.
7-Day Driving Outlook
Today
Nov 13
38° / 29°
No precip
Tomorrow
Nov 14
42° / 27°
No precip
Sun
Nov 15
47° / 28°
No precip
Mon
Nov 16
48° / 31°
No precip
Tue
Nov 17
51° / 36°
No precip
Wed
Nov 18
53° / 40°
No precip
Thu
Nov 19
53° / 51°
No precip
🗓️ Weekend Outlook
Saturday
Good to Go🌤️ Mainly clear at origin, ⛅ Partly cloudy at destination
Sunday
Good to Go🌫️ Fog at origin, ☀️ Clear sky at destination
Plan This Route
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Current Conditions
Winona, MN
29°F
Wind: 7 mph
Chicago, IL
37°F
Wind: 21 mph
Weather data updated in real-time
Driving from Winona, MN to Chicago, IL
The 252-mile drive from Winona, Minnesota to Chicago, Illinois takes approximately 5h 2m under normal conditions. Weather along this route can vary significantly, especially across open plains where severe weather and high winds can develop quickly. Route Outlook helps you find the safest time to travel by showing you weather conditions at every point along your route, timed to when you'll actually be there.
This moderate route crosses state lines from Minnesota into Illinois, connecting Winona and Chicago. A drive of 252 miles means you'll pass through multiple weather zones. Conditions at your starting point may bear little resemblance to what you'll encounter halfway through the trip.
Common Weather Hazards on This Route
- Winter storms and heavy snowfall (November through April)
- Black ice on mountain passes and bridges
Seasonal Driving Considerations
The Midwest corridor of this route is susceptible to rapid weather changes. Severe thunderstorms and tornadoes are a real threat from April through June, while winter brings heavy lake-effect snow, ice storms, and dangerously low wind chill. Flat terrain means high crosswinds can affect vehicle stability year-round, especially for taller vehicles. Spring flooding can also close highway underpasses and low-lying road segments.
Best Time to Drive Winona to Chicago
For medium-distance drives like this 252-mile route, consider starting in the early morning to arrive before afternoon storms develop. Check the 7-day forecast above to find a day with favorable conditions along the entire route.
Driving Strategy
A 252-mile drive from Winona to Chicago takes a significant part of the day. Plan at least one fuel and rest stop along the way. If your route crosses elevation changes or state lines, expect weather conditions to shift mid-trip. Monitor the segment-by-segment forecast rather than just checking destination weather. Starting early in the morning typically avoids afternoon storm development and rush-hour congestion near urban areas.
Pro Tip
Use Route Outlook's departure optimizer to find the best time to leave. Our 4D trajectory engine considers weather at each point along your route at the exact time you'll be there — not just at your destination. It also integrates live data from traffic cameras, DOT 511 feeds, and road weather sensors.
Frequently Asked Questions
How long is the drive from Winona to Chicago?
The drive is approximately 252 miles and takes about 5h 2m under normal traffic and weather conditions. Severe weather can add significant time to your trip.
What's the best day to drive this route?
Based on current forecasts, Tuesday, Nov 17 looks ideal. Clear conditions expected along the entire route
Is it safe to drive from Winona to Chicago today?
Current conditions show low risk along this route. Conditions look favorable for travel. Always stay alert and adjust speed for changing conditions.
Are there rest areas on the Winona to Chicago route?
Yes, there are 53 rest areas along this route. Facilities include restrooms, parking, and in some cases picnic areas and vending machines. Rest stops are spaced throughout the drive, so you'll never be too far from a break.
Can I see live traffic cameras on this route?
Yes, Route Outlook shows 12 live traffic cameras along this route, sourced from state DOT feeds. You can check road visibility, traffic flow, and pavement conditions in real time before and during your drive.
What highways does this route use?
This route primarily uses US-61 South, I-90 East, I-39 South. Conditions can vary between highway segments, so check live camera feeds and road condition reports for each stretch before departing.
Are there any road closures on this route right now?
There are currently 3 active incidents along this route that may affect your drive. Check the incident details above for specific locations and expected durations.
Related Driving Guides
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🛡️Road Safety Features: Real-Time Conditions for Your Route
Real-time traffic incidents from 12 states, highway message signs, road conditions, and 25,000+ traffic cameras--integrated into your route planning.
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