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Chicago

from Philadelphia

Save up to: £241

Average cost: £273

Best deal: £32

Chicago, Illinois, nestled along Lake Michigan, is famed for its bold architecture, deep-dish pizza, and jazz music. Take an architectural river cruise, visit the expansive Art Institute of Chicago, or enjoy the view from the Willis Tower Skydeck. Chicago's bustling Magnificent Mile, numerous parks, and annual events like the Chicago Air and Water Show make it a city of architectural marvels and cultural depth.

Latest deals:

7 days
£32
Tue 1 Apr - Tue 8 Apr
⌄
Philadelphia - Chicago: Tue 1/04: £16
Chicago - Philadelphia: Tue 8/04: £16
Go
5 days
£40
Thu 3 Apr - Tue 8 Apr
⌄
Philadelphia - Chicago: Thu 3/04: £24
Chicago - Philadelphia: Tue 8/04: £16
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14 days
£48
Mon 28 Apr - Mon 12 May
⌄
Philadelphia - Chicago: Mon 28/04: £24
Chicago - Philadelphia: Mon 12/05: £24
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10 days
£52
Tue 15 Apr - Fri 25 Apr
⌄
Philadelphia - Chicago: Tue 15/04: £16
Chicago - Philadelphia: Fri 25/04: £36
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14 days
£52
Tue 1 Apr - Tue 15 Apr
⌄
Philadelphia - Chicago: Tue 1/04: £16
Chicago - Philadelphia: Tue 15/04: £36
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7 days
£52
Tue 8 Apr - Tue 15 Apr
⌄
Philadelphia - Chicago: Tue 8/04: £16
Chicago - Philadelphia: Tue 15/04: £36
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15 days
£60
Thu 17 Apr - Fri 2 May
⌄
Philadelphia - Chicago: Thu 17/04: £24
Chicago - Philadelphia: Fri 2/05: £36
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11 days
£60
Mon 28 Apr - Fri 9 May
⌄
Philadelphia - Chicago: Mon 28/04: £24
Chicago - Philadelphia: Fri 9/05: £36
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10 days
£60
Fri 2 May - Mon 12 May
⌄
Philadelphia - Chicago: Fri 2/05: £36
Chicago - Philadelphia: Mon 12/05: £24
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8 days
£60
Thu 17 Apr - Fri 25 Apr
⌄
Philadelphia - Chicago: Thu 17/04: £24
Chicago - Philadelphia: Fri 25/04: £36
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7 days
£60
Mon 5 May - Mon 12 May
⌄
Philadelphia - Chicago: Mon 5/05: £36
Chicago - Philadelphia: Mon 12/05: £24
Go
12 days
£60
Thu 3 Apr - Tue 15 Apr
⌄
Philadelphia - Chicago: Thu 3/04: £24
Chicago - Philadelphia: Tue 15/04: £36
Go
7 days
£60
Mon 28 Apr - Mon 5 May
⌄
Philadelphia - Chicago: Mon 28/04: £24
Chicago - Philadelphia: Mon 5/05: £36
Go
9 days
£68
Tue 8 Apr - Thu 17 Apr
⌄
Philadelphia - Chicago: Tue 8/04: £16
Chicago - Philadelphia: Thu 17/04: £52
Go
16 days
£68
Tue 1 Apr - Thu 17 Apr
⌄
Philadelphia - Chicago: Tue 1/04: £16
Chicago - Philadelphia: Thu 17/04: £52
Go
11 days
£72
Mon 5 May - Fri 16 May
⌄
Philadelphia - Chicago: Mon 5/05: £36
Chicago - Philadelphia: Fri 16/05: £36
Go
14 days
£72
Mon 5 May - Mon 19 May
⌄
Philadelphia - Chicago: Mon 5/05: £36
Chicago - Philadelphia: Mon 19/05: £36
Go
14 days
£72
Fri 2 May - Fri 16 May
⌄
Philadelphia - Chicago: Fri 2/05: £36
Chicago - Philadelphia: Fri 16/05: £36
Go
7 days
£72
Fri 2 May - Fri 9 May
⌄
Philadelphia - Chicago: Fri 2/05: £36
Chicago - Philadelphia: Fri 9/05: £36
Go
7 days
£72
Fri 9 May - Fri 16 May
⌄
Philadelphia - Chicago: Fri 9/05: £36
Chicago - Philadelphia: Fri 16/05: £36
Go
10 days
£72
Fri 9 May - Mon 19 May
⌄
Philadelphia - Chicago: Fri 9/05: £36
Chicago - Philadelphia: Mon 19/05: £36
Go
7 days
£72
Mon 12 May - Mon 19 May
⌄
Philadelphia - Chicago: Mon 12/05: £36
Chicago - Philadelphia: Mon 19/05: £36
Go
14 days
£76
Thu 3 Apr - Thu 17 Apr
⌄
Philadelphia - Chicago: Thu 3/04: £24
Chicago - Philadelphia: Thu 17/04: £52
Go
8 days
£79
Sun 4 May - Mon 12 May
⌄
Philadelphia - Chicago: Sun 4/05: £55
Chicago - Philadelphia: Mon 12/05: £24
Go
13 days
£79
Mon 28 Apr - Sun 11 May
⌄
Philadelphia - Chicago: Mon 28/04: £24
Chicago - Philadelphia: Sun 11/05: £55
Go
5 days
£82
Tue 1 Apr - Sun 6 Apr
⌄
Philadelphia - Chicago: Tue 1/04: £16
Chicago - Philadelphia: Sun 6/04: £66
Go
12 days
£82
Tue 1 Apr - Sun 13 Apr
⌄
Philadelphia - Chicago: Tue 1/04: £16
Chicago - Philadelphia: Sun 13/04: £66
Go
5 days
£82
Tue 8 Apr - Sun 13 Apr
⌄
Philadelphia - Chicago: Tue 8/04: £16
Chicago - Philadelphia: Sun 13/04: £66
Go
9 days
£83
Mon 19 May - Wed 28 May
⌄
Philadelphia - Chicago: Mon 19/05: £36
Chicago - Philadelphia: Wed 28/05: £47
Go
16 days
£83
Mon 12 May - Wed 28 May
⌄
Philadelphia - Chicago: Mon 12/05: £36
Chicago - Philadelphia: Wed 28/05: £47
Go
16 days
£83
Mon 19 May - Wed 4 Jun
⌄
Philadelphia - Chicago: Mon 19/05: £36
Chicago - Philadelphia: Wed 4/06: £47
Go
14 days
£87
Tue 8 Apr - Tue 22 Apr
⌄
Philadelphia - Chicago: Tue 8/04: £16
Chicago - Philadelphia: Tue 22/04: £71
Go
15 days
£87
Tue 15 Apr - Wed 30 Apr
⌄
Philadelphia - Chicago: Tue 15/04: £16
Chicago - Philadelphia: Wed 30/04: £71
Go
7 days
£87
Tue 15 Apr - Tue 22 Apr
⌄
Philadelphia - Chicago: Tue 15/04: £16
Chicago - Philadelphia: Tue 22/04: £71
Go
6 days
£87
Wed 2 Apr - Tue 8 Apr
⌄
Philadelphia - Chicago: Wed 2/04: £71
Chicago - Philadelphia: Tue 8/04: £16
Go
14 days
£87
Tue 15 Apr - Tue 29 Apr
⌄
Philadelphia - Chicago: Tue 15/04: £16
Chicago - Philadelphia: Tue 29/04: £71
Go
15 days
£88
Tue 8 Apr - Wed 23 Apr
⌄
Philadelphia - Chicago: Tue 8/04: £16
Chicago - Philadelphia: Wed 23/04: £72
Go
8 days
£88
Tue 8 Apr - Wed 16 Apr
⌄
Philadelphia - Chicago: Tue 8/04: £16
Chicago - Philadelphia: Wed 16/04: £72
Go
8 days
£88
Tue 1 Apr - Wed 9 Apr
⌄
Philadelphia - Chicago: Tue 1/04: £16
Chicago - Philadelphia: Wed 9/04: £72
Go
8 days
£88
Tue 15 Apr - Wed 23 Apr
⌄
Philadelphia - Chicago: Tue 15/04: £16
Chicago - Philadelphia: Wed 23/04: £72
Go
15 days
£88
Tue 1 Apr - Wed 16 Apr
⌄
Philadelphia - Chicago: Tue 1/04: £16
Chicago - Philadelphia: Wed 16/04: £72
Go
10 days
£90
Thu 3 Apr - Sun 13 Apr
⌄
Philadelphia - Chicago: Thu 3/04: £24
Chicago - Philadelphia: Sun 13/04: £66
Go
6 days
£90
Mon 28 Apr - Sun 4 May
⌄
Philadelphia - Chicago: Mon 28/04: £24
Chicago - Philadelphia: Sun 4/05: £66
Go
8 days
£91
Sun 11 May - Mon 19 May
⌄
Philadelphia - Chicago: Sun 11/05: £55
Chicago - Philadelphia: Mon 19/05: £36
Go
9 days
£91
Fri 2 May - Sun 11 May
⌄
Philadelphia - Chicago: Fri 2/05: £36
Chicago - Philadelphia: Sun 11/05: £55
Go
6 days
£91
Mon 5 May - Sun 11 May
⌄
Philadelphia - Chicago: Mon 5/05: £36
Chicago - Philadelphia: Sun 11/05: £55
Go
12 days
£91
Sun 4 May - Fri 16 May
⌄
Philadelphia - Chicago: Sun 4/05: £55
Chicago - Philadelphia: Fri 16/05: £36
Go
5 days
£91
Sun 4 May - Fri 9 May
⌄
Philadelphia - Chicago: Sun 4/05: £55
Chicago - Philadelphia: Fri 9/05: £36
Go
5 days
£91
Sun 11 May - Fri 16 May
⌄
Philadelphia - Chicago: Sun 11/05: £55
Chicago - Philadelphia: Fri 16/05: £36
Go
15 days
£91
Sun 4 May - Mon 19 May
⌄
Philadelphia - Chicago: Sun 4/05: £55
Chicago - Philadelphia: Mon 19/05: £36
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