$231 Cheap Delta flights Orlando (MCO) to Chicago (MDW)

View $231 flight on Wed, Jun 17, 2026Opens in a new window

$231 Cheap Delta flights Orlando (MCO) to Chicago (MDW)

Prices were available within the past 7 days and start at $231 for one-way flights and $437 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sun, Jun 14 - Tue, Jun 23
MCO
Orlando
MDW
Chicago
$437 Roundtrip, found 2 days ago
$437
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Jun 14 from Orlando to Chicago, returning Tue, Jun 23, priced at $437 found 2 days ago
Delta
Wed, Jun 17 - Tue, Jun 23
MCO
Orlando
MDW
Chicago
$449 Roundtrip, found 2 days ago
$449
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Jun 17 from Orlando to Chicago, returning Tue, Jun 23, priced at $449 found 2 days ago
Delta
Wed, Jun 17 - Tue, Jun 23
MCO
Orlando
MDW
Chicago
$461 Roundtrip, found 2 days ago
$461
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Jun 17 from Orlando to Chicago, returning Tue, Jun 23, priced at $461 found 2 days ago

Find the cheapest month to fly from Orlando (MCO) to Chicago (MDW)

February is typically the cheapest month to fly

From $59 - $279 per traveler.

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $199
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $199
Flights from Orlando (MCO) to Chicago (MDW)
Origin airport
Orlando Intl.
Destination airport
Midway Intl.
Distance
1585 km
Average flight time
1 hour 49 mins