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Chicago

from Orlando

Save up to: £137

Average cost: £191

Best deal: £54

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:

4 days
£54
Wed 7 Aug - Sun 11 Aug
⌄
Orlando - Chicago: Wed 7/08: £23
Chicago - Orlando: Sun 11/08: £31
Go
5 days
£60
Thu 8 Aug - Tue 13 Aug
⌄
Orlando - Chicago: Thu 8/08: £30
Chicago - Orlando: Tue 13/08: £30
Go
3 days
£60
Sat 10 Aug - Tue 13 Aug
⌄
Orlando - Chicago: Sat 10/08: £30
Chicago - Orlando: Tue 13/08: £30
Go
2 days
£61
Tue 6 Aug - Thu 8 Aug
⌄
Orlando - Chicago: Tue 6/08: £30
Chicago - Orlando: Thu 8/08: £31
Go
4 days
£61
Tue 20 Aug - Sat 24 Aug
⌄
Orlando - Chicago: Tue 20/08: £31
Chicago - Orlando: Sat 24/08: £30
Go
5 days
£61
Mon 19 Aug - Sat 24 Aug
⌄
Orlando - Chicago: Mon 19/08: £31
Chicago - Orlando: Sat 24/08: £30
Go
5 days
£61
Wed 14 Aug - Mon 19 Aug
⌄
Orlando - Chicago: Wed 14/08: £30
Chicago - Orlando: Mon 19/08: £31
Go
4 days
£61
Wed 14 Aug - Sun 18 Aug
⌄
Orlando - Chicago: Wed 14/08: £30
Chicago - Orlando: Sun 18/08: £31
Go
5 days
£61
Tue 13 Aug - Sun 18 Aug
⌄
Orlando - Chicago: Tue 13/08: £30
Chicago - Orlando: Sun 18/08: £31
Go
2 days
£61
Tue 13 Aug - Thu 15 Aug
⌄
Orlando - Chicago: Tue 13/08: £30
Chicago - Orlando: Thu 15/08: £31
Go
2 days
£61
Wed 4 Sep - Fri 6 Sep
⌄
Orlando - Chicago: Wed 4/09: £30
Chicago - Orlando: Fri 6/09: £31
Go
5 days
£61
Sat 10 Aug - Thu 15 Aug
⌄
Orlando - Chicago: Sat 10/08: £30
Chicago - Orlando: Thu 15/08: £31
Go
4 days
£61
Fri 9 Aug - Tue 13 Aug
⌄
Orlando - Chicago: Fri 9/08: £31
Chicago - Orlando: Tue 13/08: £30
Go
5 days
£61
Tue 6 Aug - Sun 11 Aug
⌄
Orlando - Chicago: Tue 6/08: £30
Chicago - Orlando: Sun 11/08: £31
Go
3 days
£61
Thu 8 Aug - Sun 11 Aug
⌄
Orlando - Chicago: Thu 8/08: £30
Chicago - Orlando: Sun 11/08: £31
Go
4 days
£62
Sun 1 Sep - Thu 5 Sep
⌄
Orlando - Chicago: Sun 1/09: £31
Chicago - Orlando: Thu 5/09: £31
Go
5 days
£62
Tue 20 Aug - Sun 25 Aug
⌄
Orlando - Chicago: Tue 20/08: £31
Chicago - Orlando: Sun 25/08: £31
Go
3 days
£62
Tue 20 Aug - Fri 23 Aug
⌄
Orlando - Chicago: Tue 20/08: £31
Chicago - Orlando: Fri 23/08: £31
Go
2 days
£62
Tue 20 Aug - Thu 22 Aug
⌄
Orlando - Chicago: Tue 20/08: £31
Chicago - Orlando: Thu 22/08: £31
Go
4 days
£62
Mon 19 Aug - Fri 23 Aug
⌄
Orlando - Chicago: Mon 19/08: £31
Chicago - Orlando: Fri 23/08: £31
Go
3 days
£62
Mon 19 Aug - Thu 22 Aug
⌄
Orlando - Chicago: Mon 19/08: £31
Chicago - Orlando: Thu 22/08: £31
Go
2 days
£62
Mon 19 Aug - Wed 21 Aug
⌄
Orlando - Chicago: Mon 19/08: £31
Chicago - Orlando: Wed 21/08: £31
Go
5 days
£62
Fri 16 Aug - Wed 21 Aug
⌄
Orlando - Chicago: Fri 16/08: £31
Chicago - Orlando: Wed 21/08: £31
Go
4 days
£62
Fri 16 Aug - Tue 20 Aug
⌄
Orlando - Chicago: Fri 16/08: £31
Chicago - Orlando: Tue 20/08: £31
Go
3 days
£62
Fri 16 Aug - Mon 19 Aug
⌄
Orlando - Chicago: Fri 16/08: £31
Chicago - Orlando: Mon 19/08: £31
Go
2 days
£62
Fri 16 Aug - Sun 18 Aug
⌄
Orlando - Chicago: Fri 16/08: £31
Chicago - Orlando: Sun 18/08: £31
Go
5 days
£62
Thu 15 Aug - Tue 20 Aug
⌄
Orlando - Chicago: Thu 15/08: £31
Chicago - Orlando: Tue 20/08: £31
Go
5 days
£62
Sun 1 Sep - Fri 6 Sep
⌄
Orlando - Chicago: Sun 1/09: £31
Chicago - Orlando: Fri 6/09: £31
Go
3 days
£62
Thu 15 Aug - Sun 18 Aug
⌄
Orlando - Chicago: Thu 15/08: £31
Chicago - Orlando: Sun 18/08: £31
Go
2 days
£62
Fri 9 Aug - Sun 11 Aug
⌄
Orlando - Chicago: Fri 9/08: £31
Chicago - Orlando: Sun 11/08: £31
Go
3 days
£62
Mon 12 Aug - Thu 15 Aug
⌄
Orlando - Chicago: Mon 12/08: £31
Chicago - Orlando: Thu 15/08: £31
Go
4 days
£62
Thu 15 Aug - Mon 19 Aug
⌄
Orlando - Chicago: Thu 15/08: £31
Chicago - Orlando: Mon 19/08: £31
Go