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Chicago

from Orlando

Save up to: £152

Average cost: £197

Best deal: £45

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
£45
Wed 22 Oct - Sat 25 Oct
⌄
Orlando - Chicago: Wed 22/10: £29
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Chicago - Orlando: Sat 25/10: £16
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2 days
£47
Sat 1 Nov - Mon 3 Nov
⌄
Orlando - Chicago: Sat 1/11: £16
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Chicago - Orlando: Mon 3/11: £31
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2 days
£47
Sat 25 Oct - Mon 27 Oct
⌄
Orlando - Chicago: Sat 25/10: £16
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Chicago - Orlando: Mon 27/10: £31
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2 days
£47
Thu 23 Oct - Sat 25 Oct
⌄
Orlando - Chicago: Thu 23/10: £31
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Chicago - Orlando: Sat 25/10: £16
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2 days
£47
Thu 30 Oct - Sat 1 Nov
⌄
Orlando - Chicago: Thu 30/10: £31
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Chicago - Orlando: Sat 1/11: £16
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2 days
£47
Thu 13 Nov - Sat 15 Nov
⌄
Orlando - Chicago: Thu 13/11: £31
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Chicago - Orlando: Sat 15/11: £16
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2 days
£50
Sat 4 Oct - Mon 6 Oct
⌄
Orlando - Chicago: Sat 4/10: £16
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Chicago - Orlando: Mon 6/10: £34
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4 days
£53
Sat 11 Oct - Wed 15 Oct
⌄
Orlando - Chicago: Sat 11/10: £16
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Chicago - Orlando: Wed 15/10: £37
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4 days
£53
Tue 28 Oct - Sat 1 Nov
⌄
Orlando - Chicago: Tue 28/10: £37
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Chicago - Orlando: Sat 1/11: £16
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5 days
£53
Sat 25 Oct - Thu 30 Oct
⌄
Orlando - Chicago: Sat 25/10: £16
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Chicago - Orlando: Thu 30/10: £37
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4 days
£53
Sat 25 Oct - Wed 29 Oct
⌄
Orlando - Chicago: Sat 25/10: £16
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Chicago - Orlando: Wed 29/10: £37
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3 days
£53
Sat 25 Oct - Tue 28 Oct
⌄
Orlando - Chicago: Sat 25/10: £16
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Chicago - Orlando: Tue 28/10: £37
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3 days
£53
Sat 1 Nov - Tue 4 Nov
⌄
Orlando - Chicago: Sat 1/11: £16
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Chicago - Orlando: Tue 4/11: £37
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4 days
£53
Sat 1 Nov - Wed 5 Nov
⌄
Orlando - Chicago: Sat 1/11: £16
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Chicago - Orlando: Wed 5/11: £37
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3 days
£53
Wed 12 Nov - Sat 15 Nov
⌄
Orlando - Chicago: Wed 12/11: £37
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Chicago - Orlando: Sat 15/11: £16
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3 days
£53
Wed 29 Oct - Sat 1 Nov
⌄
Orlando - Chicago: Wed 29/10: £37
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Chicago - Orlando: Sat 1/11: £16
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4 days
£53
Tue 21 Oct - Sat 25 Oct
⌄
Orlando - Chicago: Tue 21/10: £37
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Chicago - Orlando: Sat 25/10: £16
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4 days
£53
Tue 11 Nov - Sat 15 Nov
⌄
Orlando - Chicago: Tue 11/11: £37
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Chicago - Orlando: Sat 15/11: £16
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2 days
£53
Thu 16 Oct - Sat 18 Oct
⌄
Orlando - Chicago: Thu 16/10: £37
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Chicago - Orlando: Sat 18/10: £16
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3 days
£53
Wed 15 Oct - Sat 18 Oct
⌄
Orlando - Chicago: Wed 15/10: £37
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Chicago - Orlando: Sat 18/10: £16
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4 days
£53
Tue 14 Oct - Sat 18 Oct
⌄
Orlando - Chicago: Tue 14/10: £37
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Chicago - Orlando: Sat 18/10: £16
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3 days
£53
Sat 11 Oct - Tue 14 Oct
⌄
Orlando - Chicago: Sat 11/10: £16
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Chicago - Orlando: Tue 14/10: £37
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3 days
£56
Sat 8 Nov - Tue 11 Nov
⌄
Orlando - Chicago: Sat 8/11: £27
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Chicago - Orlando: Tue 11/11: £29
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2 days
£56
Thu 2 Oct - Sat 4 Oct
⌄
Orlando - Chicago: Thu 2/10: £40
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Chicago - Orlando: Sat 4/10: £16
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3 days
£58
Wed 8 Oct - Sat 11 Oct
⌄
Orlando - Chicago: Wed 8/10: £29
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Chicago - Orlando: Sat 11/10: £29
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2 days
£58
Sat 8 Nov - Mon 10 Nov
⌄
Orlando - Chicago: Sat 8/11: £27
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Chicago - Orlando: Mon 10/11: £31
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2 days
£60
Sat 18 Oct - Mon 20 Oct
⌄
Orlando - Chicago: Sat 18/10: £29
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Chicago - Orlando: Mon 20/10: £31
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2 days
£60
Sat 6 Dec - Mon 8 Dec
⌄
Orlando - Chicago: Sat 6/12: £29
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Chicago - Orlando: Mon 8/12: £31
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5 days
£60
Mon 8 Dec - Sat 13 Dec
⌄
Orlando - Chicago: Mon 8/12: £31
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Chicago - Orlando: Sat 13/12: £29
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5 days
£60
Wed 22 Oct - Mon 27 Oct
⌄
Orlando - Chicago: Wed 22/10: £29
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Chicago - Orlando: Mon 27/10: £31
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2 days
£60
Wed 22 Oct - Fri 24 Oct
⌄
Orlando - Chicago: Wed 22/10: £29
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Chicago - Orlando: Fri 24/10: £31
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5 days
£60
Thu 6 Nov - Tue 11 Nov
⌄
Orlando - Chicago: Thu 6/11: £31
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Chicago - Orlando: Tue 11/11: £29
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2 days
£60
Thu 4 Dec - Sat 6 Dec
⌄
Orlando - Chicago: Thu 4/12: £31
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Chicago - Orlando: Sat 6/12: £29
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4 days
£60
Fri 7 Nov - Tue 11 Nov
⌄
Orlando - Chicago: Fri 7/11: £31
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Chicago - Orlando: Tue 11/11: £29
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4 days
£62
Thu 30 Oct - Mon 3 Nov
⌄
Orlando - Chicago: Thu 30/10: £31
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Chicago - Orlando: Mon 3/11: £31
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2 days
£62
Fri 14 Nov - Sun 16 Nov
⌄
Orlando - Chicago: Fri 14/11: £31
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Chicago - Orlando: Sun 16/11: £31
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3 days
£62
Fri 14 Nov - Mon 17 Nov
⌄
Orlando - Chicago: Fri 14/11: £31
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Chicago - Orlando: Mon 17/11: £31
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3 days
£62
Thu 4 Dec - Sun 7 Dec
⌄
Orlando - Chicago: Thu 4/12: £31
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Chicago - Orlando: Sun 7/12: £31
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2 days
£62
Fri 5 Dec - Sun 7 Dec
⌄
Orlando - Chicago: Fri 5/12: £31
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Chicago - Orlando: Sun 7/12: £31
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3 days
£62
Fri 5 Dec - Mon 8 Dec
⌄
Orlando - Chicago: Fri 5/12: £31
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Chicago - Orlando: Mon 8/12: £31
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4 days
£62
Mon 8 Dec - Fri 12 Dec
⌄
Orlando - Chicago: Mon 8/12: £31
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Chicago - Orlando: Fri 12/12: £31
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4 days
£62
Thu 4 Dec - Mon 8 Dec
⌄
Orlando - Chicago: Thu 4/12: £31
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Chicago - Orlando: Mon 8/12: £31
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4 days
£62
Thu 13 Nov - Mon 17 Nov
⌄
Orlando - Chicago: Thu 13/11: £31
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Chicago - Orlando: Mon 17/11: £31
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3 days
£62
Fri 9 Jan - Mon 12 Jan
⌄
Orlando - Chicago: Fri 9/01: £31
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Chicago - Orlando: Mon 12/01: £31
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3 days
£62
Thu 30 Oct - Sun 2 Nov
⌄
Orlando - Chicago: Thu 30/10: £31
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Chicago - Orlando: Sun 2/11: £31
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3 days
£62
Fri 7 Nov - Mon 10 Nov
⌄
Orlando - Chicago: Fri 7/11: £31
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Chicago - Orlando: Mon 10/11: £31
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2 days
£62
Fri 7 Nov - Sun 9 Nov
⌄
Orlando - Chicago: Fri 7/11: £31
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Chicago - Orlando: Sun 9/11: £31
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4 days
£62
Thu 6 Nov - Mon 10 Nov
⌄
Orlando - Chicago: Thu 6/11: £31
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Chicago - Orlando: Mon 10/11: £31
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3 days
£62
Thu 6 Nov - Sun 9 Nov
⌄
Orlando - Chicago: Thu 6/11: £31
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Chicago - Orlando: Sun 9/11: £31
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4 days
£62
Thu 23 Oct - Mon 27 Oct
⌄
Orlando - Chicago: Thu 23/10: £31
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Chicago - Orlando: Mon 27/10: £31
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3 days
£62
Fri 31 Oct - Mon 3 Nov
⌄
Orlando - Chicago: Fri 31/10: £31
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Chicago - Orlando: Mon 3/11: £31
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2 days
£62
Fri 31 Oct - Sun 2 Nov
⌄
Orlando - Chicago: Fri 31/10: £31
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Chicago - Orlando: Sun 2/11: £31
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3 days
£62
Thu 13 Nov - Sun 16 Nov
⌄
Orlando - Chicago: Thu 13/11: £31
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Chicago - Orlando: Sun 16/11: £31
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3 days
£64
Sat 4 Oct - Tue 7 Oct
⌄
Orlando - Chicago: Sat 4/10: £16
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Chicago - Orlando: Tue 7/10: £48
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4 days
£64
Sat 8 Nov - Wed 12 Nov
⌄
Orlando - Chicago: Sat 8/11: £27
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Chicago - Orlando: Wed 12/11: £37
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5 days
£64
Sat 8 Nov - Thu 13 Nov
⌄
Orlando - Chicago: Sat 8/11: £27
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Chicago - Orlando: Thu 13/11: £37
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