Boston to Chicago/Prospect Heights/Wheeling (BOS–PWK) — Airlines, Schedules & Connections

BOS Airport Page →
863 mi airlines 1/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 69 1-stop flights Verified 1d ago
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  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop

No flights match your filters.

No nonstop flights on this route. connecting options below.

✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Boston to Chicago/Prospect Heights/Wheeling
Connecting service available through multiple hubs.
1 Flights/wk 863 mi 2h 3m nonstop -1h behind 69 1-stop hubs

While no nonstop service exists between BOS and PWK, connecting options are available through 69 hubs.

Also explore BOS Routes PWK Routes BOS Live Flights PWK Live Flights BOS Delays
Connections

Connection Landscape

Beyond nonstop. 1-stop and 2-stop options for BOS to PWK.
1-STOP
One-Stop Connections
69
Hubs
~3h
Fastest
~32h
Longest
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
246
Candidates
Two-stop connections loaded in the connections tab above.
Connections computed from published schedules with minimum connection time verification. Use the interactive explorer above the fold to filter by airline, tier, and layover time.
Alternatives

Other ways to reach Chicago/Prospect Heights/Wheeling from Boston

Nearby airports with service to Chicago Executive Airport.
Metric BOS→PWK PVD→PWK HYA→PWK
Distance from BOS – 49 mi 61 mi
Nonstop airlines 0 1 1
Weekly flights 1 – –
Flight time 2h 3m 2h 22m 2h 50m
Departure OTP 100% – –
Providence/Warwick (PVD) to Chicago/Prospect Heights/Wheeling flights · Hyannis (HYA) to Chicago/Prospect Heights/Wheeling flights
Airports within 200 miles of BOS with service to Chicago Executive Airport.
Know before you go

Travel Essentials

Practical planning for this route.
Time Difference
-1h
Chicago/Prospect Heights/Wheeling is 1 hour behind Boston.
BOS: EDT · PWK: CDT

When it's 6:00 PM in Boston, it's 5:00 PM in Chicago/Prospect Heights/Wheeling.
Distance & Flight Time
863 mi / 1,389 km
Nonstop flight time is approximately 2h 3m.
Getting to BOS

MBTA Silver Line SL1 bus runs from South Station (Red Line, Amtrak) through the Ted Williams Tunnel to all Logan terminals; free from the airport, $2.40 inbound. Journey from South Station takes 15–20 minutes depending on traffic. The Blue Line Aquarium station connects to a free water taxi ($12) across the harbor to Logan; scenic but weather-dependent.Taxis from downtown Boston cost $30–45 with the Ted Williams Tunnel toll included. Ride-hails are comparable. The Sumner and Ted Williams tunnels both serve the airport; check traffic before departing, as both frequently back up. Logan is only 3 miles from downtown but tunnel congestion often extends that to 30+ minutes.

Facts

BOS–PWK Quick Facts

Key statistics for the Boston to Chicago/Prospect Heights/Wheeling route.
Route details
Distance863 mi / 1,389 km
Flight time2h 3m
Time difference-1 hour
Airlines (nonstop)0
Weekly flights1 out / 2 return
1-stop connections69 hubs
Origin: BOS
Full nameBoston Logan International Airport
IATA / ICAOBOS / KBOS
TimezoneAmerica/New_York
Passengers/yr42.2M
Elevation20 ft / 6 m
Destination: PWK
Full nameChicago Executive Airport
IATA / ICAOPWK / KPWK
TimezoneAmerica/Chicago
Elevation647 ft / 197 m
FAQ

Frequently Asked Questions

Common questions about BOS to PWK flights.
Nonstop flights from Boston Logan International Airport to Chicago Executive Airport take approximately 2h 3m. The route covers 863 miles.
There are approximately 1 nonstop flights per week from BOS to PWK. The return direction has about 2 weekly flights.
Yes, 1-stop connections are available through BDL, GYY, SUS, YYZ, GRR, PIT, MKE, LGA, CLE, CMH, IAD, PHL, MDW, ORF, ABE, IND, EWR, OMA, HYA, JFK, TYS, STL, RDU, MSP, BNA, TUL, SAV, CLT, CHS, PIE, ATL, OKC, SUA, FPO, DAL, MCO, HOU, MSY, DFW, SRQ, RSW, ADS, FLL, IAH, NAS, MIA, AUS, SAT, DEN, MBJ, SLC, PHX, BZN, PSP, VNY, LAS, SNA, SJC, BFI, SAN, OAK, LAX, ANC, SFO, BCN, SJU, TPA, PBI and HND. These options provide additional schedule flexibility.
Chicago/Prospect Heights/Wheeling is 1 hour behind Boston.
Yes, return flights from PWK to BOS are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include PVD and HYA. See the Alternatives section for a full comparison.
Click the 'Search Flights' button to check availability and prices on Google Flights. You can also compare airlines and schedules on this page to find the best option.
See the On-Time Performance section for the latest delay data at both airports. This shows departure and arrival reliability to help you plan.
Route data is updated regularly from official airline schedules. On-time performance data comes from recent airport delay snapshots.

Flights from BOS to PWK

Boston Logan International Airport (BOS) and Chicago Executive Airport (PWK) are connected through multiple connecting hub airports.

BOS to PWK Flight Duration and Schedule

Nonstop flight time from BOS to PWK ranges from 2 hours 3 minutes. The route covers a distance of 863 miles (1,389 km). There are approximately 1 weekly flights outbound and 2 return, totaling 3 flights per week in both directions.

Connecting Options and Alternatives

69 one-stop connections are available, with the fastest taking approximately 3 hours via BDL. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Providence/Warwick (PVD) and Hyannis (HYA).