$158 Cheap Delta flights Chicago (MDW) to Boston (BOS)

View $158 flight on Mon, Jun 8, 2026Opens in a new window

$158 Cheap Delta flights Chicago (MDW) to Boston (BOS)

Prices were available within the past 7 days and start at $158 for one-way flights and $316 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, Jun 8 - Fri, Jun 12
MDW
Chicago
BOS
Boston
$316 Roundtrip, found 2 days ago
$316
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Jun 8 from Chicago to Boston, returning Fri, Jun 12, priced at $316 found 2 days ago

Alternative airports near Boston

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Logan Intl. BOS. Cheapest and Closest option available. Average driving time to city center is 7 minutes. Flights from $386
BOS
Logan Intl.
CheapestClosest
Average driving time to city center7 min
Flights from $386

Find the cheapest month to fly from Chicago (MDW) to Boston (BOS)

September is typically the cheapest month to fly

From $76 - $382 per traveler.

Travel information

Origin airport
Midway Intl.
Destination airport
Logan Intl.
Airlines serving
Delta, Southwest Airlines
Popular airline
Southwest Airlines
Distance
1371 km
Average flight time
3 hours 13 mins

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