Flights from Ann Arbor to Chicago

Cheapest flights from Ann Arbor

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.

Sat, Sep 27 - Tue, Oct 7

DTW

Detroit Metropolitan Wayne County

ORD

O'Hare Intl.

$91 Roundtrip, found 2 days ago

$91

Roundtrip

found 2 days ago

Select Delta flight, departing Sat, Sep 27 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Tue, Oct 7, priced at $91 found 2 days ago

Tue, Sep 30 - Wed, Oct 1

DTW

Detroit Metropolitan Wayne County

ORD

O'Hare Intl.

$91 Roundtrip, found 2 days ago

$91

Roundtrip

found 2 days ago

Select United flight, departing Tue, Sep 30 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Wed, Oct 1, priced at $91 found 2 days ago

Sat, Sep 27 - Mon, Oct 6

DTW

Detroit Metropolitan Wayne County

ORD

O'Hare Intl.

$94 Roundtrip, found 2 days ago

$94

Roundtrip

found 2 days ago

Select Delta flight, departing Sat, Sep 27 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Mon, Oct 6, priced at $94 found 2 days ago

Mon, Sep 29 - Thu, Oct 2

DTW

Detroit Metropolitan Wayne County

ORD

O'Hare Intl.

$97 Roundtrip, found 1 day ago

$97

Roundtrip

found 1 day ago

Select American Airlines flight, departing Mon, Sep 29 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Thu, Oct 2, priced at $97 found 1 day ago

Tue, Sep 30 - Wed, Oct 1

DTW

Detroit Metropolitan Wayne County

ORD

O'Hare Intl.

$109 Roundtrip, found 2 days ago

$109

Roundtrip

found 2 days ago

Select United flight, departing Tue, Sep 30 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Wed, Oct 1, priced at $109 found 2 days ago

Tue, Sep 30 - Wed, Oct 1

DTW

Detroit Metropolitan Wayne County

ORD

O'Hare Intl.

$114 Roundtrip, found 2 days ago

$114

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Sep 30 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Wed, Oct 1, priced at $114 found 2 days ago

Tue, Sep 30 - Wed, Oct 1

DTW

Detroit Metropolitan Wayne County

ORD

O'Hare Intl.

$119 Roundtrip, found 2 days ago

$119

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Sep 30 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Wed, Oct 1, priced at $119 found 2 days ago

Sat, Sep 27 - Fri, Oct 10

DTW

Detroit Metropolitan Wayne County

ORD

O'Hare Intl.

$121 Roundtrip, found 2 days ago

$121

Roundtrip

found 2 days ago

Select Delta flight, departing Sat, Sep 27 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Fri, Oct 10, priced at $121 found 2 days ago

Tue, Sep 30 - Wed, Oct 1

DTW

Detroit Metropolitan Wayne County

ORD

O'Hare Intl.

$124 Roundtrip, found 2 days ago

$124

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Sep 30 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Wed, Oct 1, priced at $124 found 2 days ago

Sun, Sep 28 - Mon, Oct 6

DTW

Detroit Metropolitan Wayne County

ORD

O'Hare Intl.

$124 Roundtrip, found 2 days ago

$124

Roundtrip

found 2 days ago

Select Delta flight, departing Sun, Sep 28 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Mon, Oct 6, priced at $124 found 2 days ago

Tue, Sep 30 - Wed, Oct 1

DTW

Detroit Metropolitan Wayne County

ORD

O'Hare Intl.

$126 Roundtrip, found 2 days ago

$126

Roundtrip

found 2 days ago

Select United flight, departing Tue, Sep 30 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Wed, Oct 1, priced at $126 found 2 days ago

Mon, Sep 29 - Thu, Oct 2

DTW

Detroit Metropolitan Wayne County

ORD

O'Hare Intl.

$127 Roundtrip, found 1 day ago

$127

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Mon, Sep 29 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Thu, Oct 2, priced at $127 found 1 day ago

Mon, Sep 29 - Thu, Oct 2

DTW

Detroit Metropolitan Wayne County

ORD

O'Hare Intl.

$127 Roundtrip, found 1 day ago

$127

Roundtrip

found 1 day ago

Select United flight, departing Mon, Sep 29 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Thu, Oct 2, priced at $127 found 1 day ago

Mon, Sep 29 - Thu, Oct 2

DTW

Detroit Metropolitan Wayne County

ORD

O'Hare Intl.

$132 Roundtrip, found 1 day ago

$132

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Mon, Sep 29 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Thu, Oct 2, priced at $132 found 1 day ago

Tue, Sep 30 - Wed, Oct 1

DTW

Detroit Metropolitan Wayne County

ORD

O'Hare Intl.

$136 Roundtrip, found 2 days ago

$136

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Sep 30 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Wed, Oct 1, priced at $136 found 2 days ago

Tue, Sep 30 - Wed, Oct 1

DTW

Detroit Metropolitan Wayne County

ORD

O'Hare Intl.

$139 Roundtrip, found 2 days ago

$139

Roundtrip

found 2 days ago

Select United flight, departing Tue, Sep 30 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Wed, Oct 1, priced at $139 found 2 days ago

Mon, Sep 29 - Thu, Oct 2

DTW

Detroit Metropolitan Wayne County

ORD

O'Hare Intl.

$143 Roundtrip, found 1 day ago

$143

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Mon, Sep 29 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Thu, Oct 2, priced at $143 found 1 day ago

Mon, Sep 29 - Tue, Oct 7

DTW

Detroit Metropolitan Wayne County

ORD

O'Hare Intl.

$144 Roundtrip, found 2 days ago

$144

Roundtrip

found 2 days ago

Select Delta flight, departing Mon, Sep 29 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Tue, Oct 7, priced at $144 found 2 days ago

Mon, Sep 29 - Thu, Oct 2

DTW

Detroit Metropolitan Wayne County

ORD

O'Hare Intl.

$183 Roundtrip, found 1 day ago

$183

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Mon, Sep 29 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Thu, Oct 2, priced at $183 found 1 day ago

Mon, Sep 29 - Thu, Oct 2

DTW

Detroit Metropolitan Wayne County

ORD

O'Hare Intl.

$227 Roundtrip, found 1 day ago

$227

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Mon, Sep 29 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Thu, Oct 2, priced at $227 found 1 day ago