Flights from Chicago to Dundee

Cheapest flights from Chicago

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Sep 2 - Thu, Sep 11

ORD

O'Hare Intl.

MCO

Orlando Intl.

$100 Roundtrip, found 6 days ago

$100

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Tue, Sep 2 from O'Hare Intl. to Orlando Intl., returning Thu, Sep 11, priced at $100 found 6 days ago

Sun, Sep 28 - Fri, Oct 3

ORD

O'Hare Intl.

MCO

Orlando Intl.

$106 Roundtrip, found 16 hours ago

$106

Roundtrip

found 16 hours ago

Select Spirit Airlines flight, departing Sun, Sep 28 from O'Hare Intl. to Orlando Intl., returning Fri, Oct 3, priced at $106 found 16 hours ago

Fri, Sep 5 - Fri, Sep 5

ORD

O'Hare Intl.

MCO

Orlando Intl.

$111 Roundtrip, found 3 days ago

$111

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Fri, Sep 5 from O'Hare Intl. to Orlando Intl., returning Fri, Sep 5, priced at $111 found 3 days ago

Tue, Nov 4 - Sun, Nov 9

ORD

O'Hare Intl.

MCO

Orlando Intl.

$116 Roundtrip, found 19 hours ago

$116

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Tue, Nov 4 from O'Hare Intl. to Orlando Intl., returning Sun, Nov 9, priced at $116 found 19 hours ago

Sat, Aug 9 - Mon, Aug 18

ORD

O'Hare Intl.

MCO

Orlando Intl.

$124 Roundtrip, found 6 days ago

$124

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sat, Aug 9 from O'Hare Intl. to Orlando Intl., returning Mon, Aug 18, priced at $124 found 6 days ago

Fri, Oct 31 - Mon, Nov 3

ORD

O'Hare Intl.

MCO

Orlando Intl.

$126 Roundtrip, found 1 day ago

$126

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Fri, Oct 31 from O'Hare Intl. to Orlando Intl., returning Mon, Nov 3, priced at $126 found 1 day ago

Tue, Sep 2 - Thu, Sep 11

ORD

O'Hare Intl.

MCO

Orlando Intl.

$131 Roundtrip, found 6 days ago

$131

Roundtrip

found 6 days ago

Select United flight, departing Tue, Sep 2 from O'Hare Intl. to Orlando Intl., returning Thu, Sep 11, priced at $131 found 6 days ago

Tue, Sep 2 - Thu, Sep 11

ORD

O'Hare Intl.

MCO

Orlando Intl.

$131 Roundtrip, found 6 days ago

$131

Roundtrip

found 6 days ago

Select American Airlines flight, departing Tue, Sep 2 from O'Hare Intl. to Orlando Intl., returning Thu, Sep 11, priced at $131 found 6 days ago

Sun, Sep 28 - Fri, Oct 3

ORD

O'Hare Intl.

MCO

Orlando Intl.

$133 Roundtrip, found 16 hours ago

$133

Roundtrip

found 16 hours ago

Select Spirit Airlines flight, departing Sun, Sep 28 from O'Hare Intl. to Orlando Intl., returning Fri, Oct 3, priced at $133 found 16 hours ago

Tue, Oct 28 - Sun, Nov 2

ORD

O'Hare Intl.

MCO

Orlando Intl.

$136 Roundtrip, found 1 day ago

$136

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Oct 28 from O'Hare Intl. to Orlando Intl., returning Sun, Nov 2, priced at $136 found 1 day ago

Sun, Sep 28 - Fri, Oct 3

ORD

O'Hare Intl.

MCO

Orlando Intl.

$137 Roundtrip, found 16 hours ago

$137

Roundtrip

found 16 hours ago

Select Frontier Airlines flight, departing Sun, Sep 28 from O'Hare Intl. to Orlando Intl., returning Fri, Oct 3, priced at $137 found 16 hours ago

Tue, Sep 2 - Thu, Sep 11

ORD

O'Hare Intl.

MCO

Orlando Intl.

$138 Roundtrip, found 6 days ago

$138

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Tue, Sep 2 from O'Hare Intl. to Orlando Intl., returning Thu, Sep 11, priced at $138 found 6 days ago

Mon, Jul 28 - Fri, Aug 1

MDW

Midway Intl.

MCO

Orlando Intl.

$138 Roundtrip, found 6 days ago

$138

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Mon, Jul 28 from Midway Intl. to Orlando Intl., returning Fri, Aug 1, priced at $138 found 6 days ago

Sun, Aug 10 - Thu, Aug 14

ORD

O'Hare Intl.

MCO

Orlando Intl.

$140 Roundtrip, found 4 days ago

$140

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Sun, Aug 10 from O'Hare Intl. to Orlando Intl., returning Thu, Aug 14, priced at $140 found 4 days ago

Tue, Sep 2 - Thu, Sep 11

ORD

O'Hare Intl.

MCO

Orlando Intl.

$142 Roundtrip, found 6 days ago

$142

Roundtrip

found 6 days ago

Select United flight, departing Tue, Sep 2 from O'Hare Intl. to Orlando Intl., returning Thu, Sep 11, priced at $142 found 6 days ago

Sun, Sep 28 - Fri, Oct 3

ORD

O'Hare Intl.

MCO

Orlando Intl.

$144 Roundtrip, found 16 hours ago

$144

Roundtrip

found 16 hours ago

Select Spirit Airlines flight, departing Sun, Sep 28 from O'Hare Intl. to Orlando Intl., returning Fri, Oct 3, priced at $144 found 16 hours ago

Sat, Sep 13 - Fri, Sep 19

MDW

Midway Intl.

MCO

Orlando Intl.

$146 Roundtrip, found 6 days ago

$146

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sat, Sep 13 from Midway Intl. to Orlando Intl., returning Fri, Sep 19, priced at $146 found 6 days ago

Tue, Sep 16 - Tue, Sep 16

MDW

Midway Intl.

MCO

Orlando Intl.

$191 Roundtrip, found 6 days ago

$191

Roundtrip

found 6 days ago

Select Delta flight, departing Tue, Sep 16 from Midway Intl. to Orlando Intl., returning Tue, Sep 16, priced at $191 found 6 days ago

Wed, Nov 19 - Sun, Nov 23

ORD

O'Hare Intl.

MCO

Orlando Intl.

$217 Roundtrip, found 6 days ago

$217

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Wed, Nov 19 from O'Hare Intl. to Orlando Intl., returning Sun, Nov 23, priced at $217 found 6 days ago

Mon, Oct 13 - Fri, Oct 24

ORD

O'Hare Intl.

MCO

Orlando Intl.

$443 Roundtrip, found 5 days ago

$443

Roundtrip

found 5 days ago

Select Sun Country Airlines flight, departing Mon, Oct 13 from O'Hare Intl. to Orlando Intl., returning Fri, Oct 24, priced at $443 found 5 days ago