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Chicago

from Philadelphia

Save up to: £170

Average cost: £214

Best deal: £44

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:

5 days
£44
Sun 18 Jan - Fri 23 Jan
⌄
Philadelphia - Chicago: Sun 18/01: £22
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Chicago - Philadelphia: Fri 23/01: £22
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4 days
£44
Mon 26 Jan - Fri 30 Jan
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Philadelphia - Chicago: Mon 26/01: £22
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Chicago - Philadelphia: Fri 30/01: £22
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4 days
£44
Mon 2 Feb - Fri 6 Feb
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Philadelphia - Chicago: Mon 2/02: £22
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Chicago - Philadelphia: Fri 6/02: £22
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3 days
£44
Fri 6 Feb - Mon 9 Feb
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Philadelphia - Chicago: Fri 6/02: £22
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Chicago - Philadelphia: Mon 9/02: £22
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4 days
£44
Mon 23 Feb - Fri 27 Feb
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Philadelphia - Chicago: Mon 23/02: £22
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Chicago - Philadelphia: Fri 27/02: £22
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4 days
£56
Mon 24 Nov - Fri 28 Nov
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Philadelphia - Chicago: Mon 24/11: £22
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Chicago - Philadelphia: Fri 28/11: £34
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5 days
£60
Fri 20 Feb - Wed 25 Feb
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Philadelphia - Chicago: Fri 20/02: £22
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Chicago - Philadelphia: Wed 25/02: £38
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2 days
£60
Wed 21 Jan - Fri 23 Jan
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Philadelphia - Chicago: Wed 21/01: £38
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Chicago - Philadelphia: Fri 23/01: £22
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4 days
£60
Fri 23 Jan - Tue 27 Jan
⌄
Philadelphia - Chicago: Fri 23/01: £22
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Chicago - Philadelphia: Tue 27/01: £38
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4 days
£60
Fri 27 Feb - Tue 3 Mar
⌄
Philadelphia - Chicago: Fri 27/02: £22
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Chicago - Philadelphia: Tue 3/03: £38
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2 days
£60
Mon 26 Jan - Wed 28 Jan
⌄
Philadelphia - Chicago: Mon 26/01: £22
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Chicago - Philadelphia: Wed 28/01: £38
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2 days
£60
Wed 25 Feb - Fri 27 Feb
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Philadelphia - Chicago: Wed 25/02: £38
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Chicago - Philadelphia: Fri 27/02: £22
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5 days
£60
Mon 26 Jan - Sat 31 Jan
⌄
Philadelphia - Chicago: Mon 26/01: £22
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Chicago - Philadelphia: Sat 31/01: £38
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3 days
£60
Tue 27 Jan - Fri 30 Jan
⌄
Philadelphia - Chicago: Tue 27/01: £38
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Chicago - Philadelphia: Fri 30/01: £22
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2 days
£60
Wed 28 Jan - Fri 30 Jan
⌄
Philadelphia - Chicago: Wed 28/01: £38
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Chicago - Philadelphia: Fri 30/01: £22
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5 days
£60
Wed 28 Jan - Mon 2 Feb
⌄
Philadelphia - Chicago: Wed 28/01: £38
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Chicago - Philadelphia: Mon 2/02: £22
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2 days
£60
Sat 31 Jan - Mon 2 Feb
⌄
Philadelphia - Chicago: Sat 31/01: £38
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Chicago - Philadelphia: Mon 2/02: £22
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2 days
£60
Mon 2 Feb - Wed 4 Feb
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Philadelphia - Chicago: Mon 2/02: £22
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Chicago - Philadelphia: Wed 4/02: £38
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3 days
£60
Tue 24 Feb - Fri 27 Feb
⌄
Philadelphia - Chicago: Tue 24/02: £38
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Chicago - Philadelphia: Fri 27/02: £22
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5 days
£60
Mon 2 Feb - Sat 7 Feb
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Philadelphia - Chicago: Mon 2/02: £22
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Chicago - Philadelphia: Sat 7/02: £38
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3 days
£60
Tue 3 Feb - Fri 6 Feb
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Philadelphia - Chicago: Tue 3/02: £38
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Chicago - Philadelphia: Fri 6/02: £22
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3 days
£60
Tue 20 Jan - Fri 23 Jan
⌄
Philadelphia - Chicago: Tue 20/01: £38
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Chicago - Philadelphia: Fri 23/01: £22
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5 days
£60
Wed 4 Feb - Mon 9 Feb
⌄
Philadelphia - Chicago: Wed 4/02: £38
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Chicago - Philadelphia: Mon 9/02: £22
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5 days
£60
Mon 23 Feb - Sat 28 Feb
⌄
Philadelphia - Chicago: Mon 23/02: £22
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Chicago - Philadelphia: Sat 28/02: £38
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4 days
£60
Fri 6 Feb - Tue 10 Feb
⌄
Philadelphia - Chicago: Fri 6/02: £22
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Chicago - Philadelphia: Tue 10/02: £38
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5 days
£60
Fri 6 Feb - Wed 11 Feb
⌄
Philadelphia - Chicago: Fri 6/02: £22
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Chicago - Philadelphia: Wed 11/02: £38
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2 days
£60
Sat 7 Feb - Mon 9 Feb
⌄
Philadelphia - Chicago: Sat 7/02: £38
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Chicago - Philadelphia: Mon 9/02: £22
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2 days
£60
Mon 9 Feb - Wed 11 Feb
⌄
Philadelphia - Chicago: Mon 9/02: £22
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Chicago - Philadelphia: Wed 11/02: £38
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5 days
£60
Mon 9 Feb - Sat 14 Feb
⌄
Philadelphia - Chicago: Mon 9/02: £22
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Chicago - Philadelphia: Sat 14/02: £38
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4 days
£60
Fri 20 Feb - Tue 24 Feb
⌄
Philadelphia - Chicago: Fri 20/02: £22
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Chicago - Philadelphia: Tue 24/02: £38
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2 days
£60
Mon 23 Feb - Wed 25 Feb
⌄
Philadelphia - Chicago: Mon 23/02: £22
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Chicago - Philadelphia: Wed 25/02: £38
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2 days
£60
Wed 4 Feb - Fri 6 Feb
⌄
Philadelphia - Chicago: Wed 4/02: £38
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Chicago - Philadelphia: Fri 6/02: £22
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5 days
£60
Fri 23 Jan - Wed 28 Jan
⌄
Philadelphia - Chicago: Fri 23/01: £22
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Chicago - Philadelphia: Wed 28/01: £38
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5 days
£60
Fri 27 Feb - Wed 4 Mar
⌄
Philadelphia - Chicago: Fri 27/02: £22
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Chicago - Philadelphia: Wed 4/03: £38
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5 days
£60
Wed 17 Dec - Mon 22 Dec
⌄
Philadelphia - Chicago: Wed 17/12: £38
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Chicago - Philadelphia: Mon 22/12: £22
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2 days
£60
Tue 6 Jan - Thu 8 Jan
⌄
Philadelphia - Chicago: Tue 6/01: £38
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Chicago - Philadelphia: Thu 8/01: £22
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5 days
£60
Wed 7 Jan - Mon 12 Jan
⌄
Philadelphia - Chicago: Wed 7/01: £38
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Chicago - Philadelphia: Mon 12/01: £22
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2 days
£60
Sat 10 Jan - Mon 12 Jan
⌄
Philadelphia - Chicago: Sat 10/01: £38
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Chicago - Philadelphia: Mon 12/01: £22
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2 days
£60
Sun 11 Jan - Tue 13 Jan
⌄
Philadelphia - Chicago: Sun 11/01: £22
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Chicago - Philadelphia: Tue 13/01: £38
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3 days
£60
Sun 11 Jan - Wed 14 Jan
⌄
Philadelphia - Chicago: Sun 11/01: £22
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Chicago - Philadelphia: Wed 14/01: £38
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5 days
£60
Mon 8 Dec - Sat 13 Dec
⌄
Philadelphia - Chicago: Mon 8/12: £22
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Chicago - Philadelphia: Sat 13/12: £38
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2 days
£60
Mon 12 Jan - Wed 14 Jan
⌄
Philadelphia - Chicago: Mon 12/01: £22
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Chicago - Philadelphia: Wed 14/01: £38
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2 days
£60
Mon 8 Dec - Wed 10 Dec
⌄
Philadelphia - Chicago: Mon 8/12: £22
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Chicago - Philadelphia: Wed 10/12: £38
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2 days
£60
Mon 15 Dec - Wed 17 Dec
⌄
Philadelphia - Chicago: Mon 15/12: £22
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Chicago - Philadelphia: Wed 17/12: £38
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5 days
£60
Tue 13 Jan - Sun 18 Jan
⌄
Philadelphia - Chicago: Tue 13/01: £38
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Chicago - Philadelphia: Sun 18/01: £22
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3 days
£60
Sun 18 Jan - Wed 21 Jan
⌄
Philadelphia - Chicago: Sun 18/01: £22
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Chicago - Philadelphia: Wed 21/01: £38
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4 days
£60
Wed 14 Jan - Sun 18 Jan
⌄
Philadelphia - Chicago: Wed 14/01: £38
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Chicago - Philadelphia: Sun 18/01: £22
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2 days
£60
Sun 18 Jan - Tue 20 Jan
⌄
Philadelphia - Chicago: Sun 18/01: £22
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Chicago - Philadelphia: Tue 20/01: £38
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5 days
£60
Mon 12 Jan - Sat 17 Jan
⌄
Philadelphia - Chicago: Mon 12/01: £22
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Chicago - Philadelphia: Sat 17/01: £38
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3 days
£64
Fri 20 Feb - Mon 23 Feb
⌄
Philadelphia - Chicago: Fri 20/02: £22
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Chicago - Philadelphia: Mon 23/02: £42
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3 days
£65
Mon 12 Jan - Thu 15 Jan
⌄
Philadelphia - Chicago: Mon 12/01: £22
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Chicago - Philadelphia: Thu 15/01: £43
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3 days
£65
Mon 23 Feb - Thu 26 Feb
⌄
Philadelphia - Chicago: Mon 23/02: £22
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Chicago - Philadelphia: Thu 26/02: £43
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3 days
£65
Mon 9 Feb - Thu 12 Feb
⌄
Philadelphia - Chicago: Mon 9/02: £22
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Chicago - Philadelphia: Thu 12/02: £43
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2 days
£65
Mon 22 Dec - Wed 24 Dec
⌄
Philadelphia - Chicago: Mon 22/12: £43
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Chicago - Philadelphia: Wed 24/12: £22
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5 days
£65
Wed 31 Dec - Mon 5 Jan
⌄
Philadelphia - Chicago: Wed 31/12: £22
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Chicago - Philadelphia: Mon 5/01: £43
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3 days
£65
Fri 23 Jan - Mon 26 Jan
⌄
Philadelphia - Chicago: Fri 23/01: £22
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Chicago - Philadelphia: Mon 26/01: £43
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4 days
£65
Thu 8 Jan - Mon 12 Jan
⌄
Philadelphia - Chicago: Thu 8/01: £43
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Chicago - Philadelphia: Mon 12/01: £22
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4 days
£65
Sun 18 Jan - Thu 22 Jan
⌄
Philadelphia - Chicago: Sun 18/01: £22
Go
Chicago - Philadelphia: Thu 22/01: £43
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3 days
£65
Fri 27 Feb - Mon 2 Mar
⌄
Philadelphia - Chicago: Fri 27/02: £22
Go
Chicago - Philadelphia: Mon 2/03: £43
Go
3 days
£65
Thu 15 Jan - Sun 18 Jan
⌄
Philadelphia - Chicago: Thu 15/01: £43
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Chicago - Philadelphia: Sun 18/01: £22
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3 days
£65
Mon 15 Dec - Thu 18 Dec
⌄
Philadelphia - Chicago: Mon 15/12: £22
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Chicago - Philadelphia: Thu 18/12: £43
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4 days
£65
Sun 11 Jan - Thu 15 Jan
⌄
Philadelphia - Chicago: Sun 11/01: £22
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Chicago - Philadelphia: Thu 15/01: £43
Go
3 days
£65
Mon 26 Jan - Thu 29 Jan
⌄
Philadelphia - Chicago: Mon 26/01: £22
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Chicago - Philadelphia: Thu 29/01: £43
Go
3 days
£65
Mon 8 Dec - Thu 11 Dec
⌄
Philadelphia - Chicago: Mon 8/12: £22
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Chicago - Philadelphia: Thu 11/12: £43
Go
4 days
£65
Thu 29 Jan - Mon 2 Feb
⌄
Philadelphia - Chicago: Thu 29/01: £43
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Chicago - Philadelphia: Mon 2/02: £22
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4 days
£65
Thu 5 Feb - Mon 9 Feb
⌄
Philadelphia - Chicago: Thu 5/02: £43
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Chicago - Philadelphia: Mon 9/02: £22
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3 days
£65
Mon 2 Feb - Thu 5 Feb
⌄
Philadelphia - Chicago: Mon 2/02: £22
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Chicago - Philadelphia: Thu 5/02: £43
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4 days
£69
Fri 12 Dec - Tue 16 Dec
⌄
Philadelphia - Chicago: Fri 12/12: £31
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Chicago - Philadelphia: Tue 16/12: £38
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3 days
£69
Fri 9 Jan - Mon 12 Jan
⌄
Philadelphia - Chicago: Fri 9/01: £47
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Chicago - Philadelphia: Mon 12/01: £22
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3 days
£69
Fri 30 Jan - Mon 2 Feb
⌄
Philadelphia - Chicago: Fri 30/01: £47
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Chicago - Philadelphia: Mon 2/02: £22
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5 days
£69
Fri 12 Dec - Wed 17 Dec
⌄
Philadelphia - Chicago: Fri 12/12: £31
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Chicago - Philadelphia: Wed 17/12: £38
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4 days
£70
Mon 9 Feb - Fri 13 Feb
⌄
Philadelphia - Chicago: Mon 9/02: £22
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Chicago - Philadelphia: Fri 13/02: £48
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3 days
£70
Mon 5 Jan - Thu 8 Jan
⌄
Philadelphia - Chicago: Mon 5/01: £48
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Chicago - Philadelphia: Thu 8/01: £22
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5 days
£70
Sun 11 Jan - Fri 16 Jan
⌄
Philadelphia - Chicago: Sun 11/01: £22
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Chicago - Philadelphia: Fri 16/01: £48
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4 days
£70
Mon 12 Jan - Fri 16 Jan
⌄
Philadelphia - Chicago: Mon 12/01: £22
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Chicago - Philadelphia: Fri 16/01: £48
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2 days
£70
Fri 16 Jan - Sun 18 Jan
⌄
Philadelphia - Chicago: Fri 16/01: £48
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Chicago - Philadelphia: Sun 18/01: £22
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4 days
£70
Mon 19 Jan - Fri 23 Jan
⌄
Philadelphia - Chicago: Mon 19/01: £48
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Chicago - Philadelphia: Fri 23/01: £22
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