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Chicago

from Philadelphia

Save up to: £103

Average cost: £145

Best deal: £42

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:

3 days
£42
Sun 26 May - Wed 29 May
⌄
Philadelphia - Chicago: Sun 26/05: £19
Chicago - Philadelphia: Wed 29/05: £23
Go
3 days
£46
Sat 3 Aug - Tue 6 Aug
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Philadelphia - Chicago: Sat 3/08: £23
Chicago - Philadelphia: Tue 6/08: £23
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4 days
£46
Sat 3 Aug - Wed 7 Aug
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Philadelphia - Chicago: Sat 3/08: £23
Chicago - Philadelphia: Wed 7/08: £23
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4 days
£46
Tue 6 Aug - Sat 10 Aug
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Philadelphia - Chicago: Tue 6/08: £23
Chicago - Philadelphia: Sat 10/08: £23
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3 days
£46
Wed 7 Aug - Sat 10 Aug
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Philadelphia - Chicago: Wed 7/08: £23
Chicago - Philadelphia: Sat 10/08: £23
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4 days
£46
Tue 13 Aug - Sat 17 Aug
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Philadelphia - Chicago: Tue 13/08: £23
Chicago - Philadelphia: Sat 17/08: £23
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3 days
£46
Wed 14 Aug - Sat 17 Aug
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Philadelphia - Chicago: Wed 14/08: £23
Chicago - Philadelphia: Sat 17/08: £23
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3 days
£46
Sat 24 Aug - Tue 27 Aug
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Philadelphia - Chicago: Sat 24/08: £23
Chicago - Philadelphia: Tue 27/08: £23
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4 days
£46
Sat 24 Aug - Wed 28 Aug
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Philadelphia - Chicago: Sat 24/08: £23
Chicago - Philadelphia: Wed 28/08: £23
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3 days
£46
Sat 31 Aug - Tue 3 Sep
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Philadelphia - Chicago: Sat 31/08: £23
Chicago - Philadelphia: Tue 3/09: £23
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4 days
£46
Sat 31 Aug - Wed 4 Sep
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Philadelphia - Chicago: Sat 31/08: £23
Chicago - Philadelphia: Wed 4/09: £23
Go
4 days
£46
Tue 3 Sep - Sat 7 Sep
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Philadelphia - Chicago: Tue 3/09: £23
Chicago - Philadelphia: Sat 7/09: £23
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3 days
£46
Wed 4 Sep - Sat 7 Sep
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Philadelphia - Chicago: Wed 4/09: £23
Chicago - Philadelphia: Sat 7/09: £23
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4 days
£46
Sat 7 Sep - Wed 11 Sep
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Philadelphia - Chicago: Sat 7/09: £23
Chicago - Philadelphia: Wed 11/09: £23
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4 days
£46
Tue 10 Sep - Sat 14 Sep
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Philadelphia - Chicago: Tue 10/09: £23
Chicago - Philadelphia: Sat 14/09: £23
Go
3 days
£46
Wed 11 Sep - Sat 14 Sep
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Philadelphia - Chicago: Wed 11/09: £23
Chicago - Philadelphia: Sat 14/09: £23
Go
3 days
£46
Sat 14 Sep - Tue 17 Sep
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Philadelphia - Chicago: Sat 14/09: £23
Chicago - Philadelphia: Tue 17/09: £23
Go
4 days
£46
Sat 14 Sep - Wed 18 Sep
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Philadelphia - Chicago: Sat 14/09: £23
Chicago - Philadelphia: Wed 18/09: £23
Go
4 days
£46
Tue 17 Sep - Sat 21 Sep
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Philadelphia - Chicago: Tue 17/09: £23
Chicago - Philadelphia: Sat 21/09: £23
Go
3 days
£46
Wed 18 Sep - Sat 21 Sep
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Philadelphia - Chicago: Wed 18/09: £23
Chicago - Philadelphia: Sat 21/09: £23
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4 days
£46
Tue 24 Sep - Sat 28 Sep
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Philadelphia - Chicago: Tue 24/09: £23
Chicago - Philadelphia: Sat 28/09: £23
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3 days
£46
Sat 28 Sep - Tue 1 Oct
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Philadelphia - Chicago: Sat 28/09: £23
Chicago - Philadelphia: Tue 1/10: £23
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4 days
£46
Sat 28 Sep - Wed 2 Oct
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Philadelphia - Chicago: Sat 28/09: £23
Chicago - Philadelphia: Wed 2/10: £23
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4 days
£46
Tue 1 Oct - Sat 5 Oct
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Philadelphia - Chicago: Tue 1/10: £23
Chicago - Philadelphia: Sat 5/10: £23
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4 days
£46
Sat 27 Jul - Wed 31 Jul
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Philadelphia - Chicago: Sat 27/07: £23
Chicago - Philadelphia: Wed 31/07: £23
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3 days
£46
Sat 27 Jul - Tue 30 Jul
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Philadelphia - Chicago: Sat 27/07: £23
Chicago - Philadelphia: Tue 30/07: £23
Go
3 days
£46
Wed 24 Jul - Sat 27 Jul
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Philadelphia - Chicago: Wed 24/07: £23
Chicago - Philadelphia: Sat 27/07: £23
Go
4 days
£46
Tue 23 Jul - Sat 27 Jul
⌄
Philadelphia - Chicago: Tue 23/07: £23
Chicago - Philadelphia: Sat 27/07: £23
Go
4 days
£46
Tue 28 May - Sat 1 Jun
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Philadelphia - Chicago: Tue 28/05: £23
Chicago - Philadelphia: Sat 1/06: £23
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3 days
£46
Wed 29 May - Sat 1 Jun
⌄
Philadelphia - Chicago: Wed 29/05: £23
Chicago - Philadelphia: Sat 1/06: £23
Go
3 days
£46
Sat 1 Jun - Tue 4 Jun
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Philadelphia - Chicago: Sat 1/06: £23
Chicago - Philadelphia: Tue 4/06: £23
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4 days
£46
Sat 1 Jun - Wed 5 Jun
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Philadelphia - Chicago: Sat 1/06: £23
Chicago - Philadelphia: Wed 5/06: £23
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3 days
£46
Sat 8 Jun - Tue 11 Jun
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Philadelphia - Chicago: Sat 8/06: £23
Chicago - Philadelphia: Tue 11/06: £23
Go
4 days
£46
Sat 8 Jun - Wed 12 Jun
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Philadelphia - Chicago: Sat 8/06: £23
Chicago - Philadelphia: Wed 12/06: £23
Go
4 days
£46
Tue 11 Jun - Sat 15 Jun
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Philadelphia - Chicago: Tue 11/06: £23
Chicago - Philadelphia: Sat 15/06: £23
Go
3 days
£46
Wed 12 Jun - Sat 15 Jun
⌄
Philadelphia - Chicago: Wed 12/06: £23
Chicago - Philadelphia: Sat 15/06: £23
Go
3 days
£46
Sat 15 Jun - Tue 18 Jun
⌄
Philadelphia - Chicago: Sat 15/06: £23
Chicago - Philadelphia: Tue 18/06: £23
Go
4 days
£46
Sat 15 Jun - Wed 19 Jun
⌄
Philadelphia - Chicago: Sat 15/06: £23
Chicago - Philadelphia: Wed 19/06: £23
Go
3 days
£46
Wed 19 Jun - Sat 22 Jun
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Philadelphia - Chicago: Wed 19/06: £23
Chicago - Philadelphia: Sat 22/06: £23
Go
3 days
£46
Wed 2 Oct - Sat 5 Oct
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Philadelphia - Chicago: Wed 2/10: £23
Chicago - Philadelphia: Sat 5/10: £23
Go
4 days
£46
Tue 25 Jun - Sat 29 Jun
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Philadelphia - Chicago: Tue 25/06: £23
Chicago - Philadelphia: Sat 29/06: £23
Go
3 days
£46
Sat 29 Jun - Tue 2 Jul
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Philadelphia - Chicago: Sat 29/06: £23
Chicago - Philadelphia: Tue 2/07: £23
Go
4 days
£46
Sat 29 Jun - Wed 3 Jul
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Philadelphia - Chicago: Sat 29/06: £23
Chicago - Philadelphia: Wed 3/07: £23
Go
3 days
£46
Sat 6 Jul - Tue 9 Jul
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Philadelphia - Chicago: Sat 6/07: £23
Chicago - Philadelphia: Tue 9/07: £23
Go
4 days
£46
Sat 6 Jul - Wed 10 Jul
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Philadelphia - Chicago: Sat 6/07: £23
Chicago - Philadelphia: Wed 10/07: £23
Go
4 days
£46
Tue 9 Jul - Sat 13 Jul
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Philadelphia - Chicago: Tue 9/07: £23
Chicago - Philadelphia: Sat 13/07: £23
Go
3 days
£46
Wed 10 Jul - Sat 13 Jul
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Philadelphia - Chicago: Wed 10/07: £23
Chicago - Philadelphia: Sat 13/07: £23
Go
3 days
£46
Sat 13 Jul - Tue 16 Jul
⌄
Philadelphia - Chicago: Sat 13/07: £23
Chicago - Philadelphia: Tue 16/07: £23
Go
4 days
£46
Sat 13 Jul - Wed 17 Jul
⌄
Philadelphia - Chicago: Sat 13/07: £23
Chicago - Philadelphia: Wed 17/07: £23
Go
4 days
£46
Tue 16 Jul - Sat 20 Jul
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Philadelphia - Chicago: Tue 16/07: £23
Chicago - Philadelphia: Sat 20/07: £23
Go
3 days
£46
Sat 20 Jul - Tue 23 Jul
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Philadelphia - Chicago: Sat 20/07: £23
Chicago - Philadelphia: Tue 23/07: £23
Go
4 days
£46
Sat 20 Jul - Wed 24 Jul
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Philadelphia - Chicago: Sat 20/07: £23
Chicago - Philadelphia: Wed 24/07: £23
Go
3 days
£46
Wed 26 Jun - Sat 29 Jun
⌄
Philadelphia - Chicago: Wed 26/06: £23
Chicago - Philadelphia: Sat 29/06: £23
Go
3 days
£46
Sat 5 Oct - Tue 8 Oct
⌄
Philadelphia - Chicago: Sat 5/10: £23
Chicago - Philadelphia: Tue 8/10: £23
Go