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Chicago

from Orlando

Save up to: £138

Average cost: £191

Best deal: £53

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
£53
Tue 28 May - Tue 4 Jun
⌄
Orlando - Chicago: Tue 28/05: £23
Chicago - Orlando: Tue 4/06: £30
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8 days
£53
Tue 28 May - Wed 5 Jun
⌄
Orlando - Chicago: Tue 28/05: £23
Chicago - Orlando: Wed 5/06: £30
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6 days
£53
Wed 29 May - Tue 4 Jun
⌄
Orlando - Chicago: Wed 29/05: £23
Chicago - Orlando: Tue 4/06: £30
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7 days
£53
Wed 29 May - Wed 5 Jun
⌄
Orlando - Chicago: Wed 29/05: £23
Chicago - Orlando: Wed 5/06: £30
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6 days
£53
Wed 7 Aug - Tue 13 Aug
⌄
Orlando - Chicago: Wed 7/08: £23
Chicago - Orlando: Tue 13/08: £30
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16 days
£54
Wed 7 Aug - Fri 23 Aug
⌄
Orlando - Chicago: Wed 7/08: £23
Chicago - Orlando: Fri 23/08: £31
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15 days
£54
Wed 7 Aug - Thu 22 Aug
⌄
Orlando - Chicago: Wed 7/08: £23
Chicago - Orlando: Thu 22/08: £31
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13 days
£54
Wed 7 Aug - Tue 20 Aug
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Orlando - Chicago: Wed 7/08: £23
Chicago - Orlando: Tue 20/08: £31
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12 days
£54
Wed 7 Aug - Mon 19 Aug
⌄
Orlando - Chicago: Wed 7/08: £23
Chicago - Orlando: Mon 19/08: £31
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11 days
£54
Wed 7 Aug - Sun 18 Aug
⌄
Orlando - Chicago: Wed 7/08: £23
Chicago - Orlando: Sun 18/08: £31
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8 days
£54
Wed 7 Aug - Thu 15 Aug
⌄
Orlando - Chicago: Wed 7/08: £23
Chicago - Orlando: Thu 15/08: £31
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14 days
£54
Wed 7 Aug - Wed 21 Aug
⌄
Orlando - Chicago: Wed 7/08: £23
Chicago - Orlando: Wed 21/08: £31
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10 days
£58
Wed 7 Aug - Sat 17 Aug
⌄
Orlando - Chicago: Wed 7/08: £23
Chicago - Orlando: Sat 17/08: £35
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14 days
£58
Wed 10 Jul - Wed 24 Jul
⌄
Orlando - Chicago: Wed 10/07: £23
Chicago - Orlando: Wed 24/07: £35
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11 days
£60
Tue 13 Aug - Sat 24 Aug
⌄
Orlando - Chicago: Tue 13/08: £30
Chicago - Orlando: Sat 24/08: £30
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10 days
£60
Wed 14 Aug - Sat 24 Aug
⌄
Orlando - Chicago: Wed 14/08: £30
Chicago - Orlando: Sat 24/08: £30
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16 days
£60
Thu 8 Aug - Sat 24 Aug
⌄
Orlando - Chicago: Thu 8/08: £30
Chicago - Orlando: Sat 24/08: £30
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14 days
£60
Sat 10 Aug - Sat 24 Aug
⌄
Orlando - Chicago: Sat 10/08: £30
Chicago - Orlando: Sat 24/08: £30
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7 days
£60
Tue 6 Aug - Tue 13 Aug
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Orlando - Chicago: Tue 6/08: £30
Chicago - Orlando: Tue 13/08: £30
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5 days
£60
Thu 8 Aug - Tue 13 Aug
⌄
Orlando - Chicago: Thu 8/08: £30
Chicago - Orlando: Tue 13/08: £30
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8 days
£61
Tue 13 Aug - Wed 21 Aug
⌄
Orlando - Chicago: Tue 13/08: £30
Chicago - Orlando: Wed 21/08: £31
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7 days
£61
Tue 13 Aug - Tue 20 Aug
⌄
Orlando - Chicago: Tue 13/08: £30
Chicago - Orlando: Tue 20/08: £31
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9 days
£61
Wed 14 Aug - Fri 23 Aug
⌄
Orlando - Chicago: Wed 14/08: £30
Chicago - Orlando: Fri 23/08: £31
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9 days
£61
Tue 13 Aug - Thu 22 Aug
⌄
Orlando - Chicago: Tue 13/08: £30
Chicago - Orlando: Thu 22/08: £31
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12 days
£61
Mon 12 Aug - Sat 24 Aug
⌄
Orlando - Chicago: Mon 12/08: £31
Chicago - Orlando: Sat 24/08: £30
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15 days
£61
Sat 10 Aug - Sun 25 Aug
⌄
Orlando - Chicago: Sat 10/08: £30
Chicago - Orlando: Sun 25/08: £31
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13 days
£61
Sat 10 Aug - Fri 23 Aug
⌄
Orlando - Chicago: Sat 10/08: £30
Chicago - Orlando: Fri 23/08: £31
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12 days
£61
Sat 10 Aug - Thu 22 Aug
⌄
Orlando - Chicago: Sat 10/08: £30
Chicago - Orlando: Thu 22/08: £31
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6 days
£61
Tue 13 Aug - Mon 19 Aug
⌄
Orlando - Chicago: Tue 13/08: £30
Chicago - Orlando: Mon 19/08: £31
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5 days
£61
Tue 13 Aug - Sun 18 Aug
⌄
Orlando - Chicago: Tue 13/08: £30
Chicago - Orlando: Sun 18/08: £31
Go
13 days
£61
Tue 13 Aug - Mon 26 Aug
⌄
Orlando - Chicago: Tue 13/08: £30
Chicago - Orlando: Mon 26/08: £31
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12 days
£61
Tue 13 Aug - Sun 25 Aug
⌄
Orlando - Chicago: Tue 13/08: £30
Chicago - Orlando: Sun 25/08: £31
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5 days
£61
Wed 14 Aug - Mon 19 Aug
⌄
Orlando - Chicago: Wed 14/08: £30
Chicago - Orlando: Mon 19/08: £31
Go
6 days
£61
Wed 14 Aug - Tue 20 Aug
⌄
Orlando - Chicago: Wed 14/08: £30
Chicago - Orlando: Tue 20/08: £31
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5 days
£61
Mon 19 Aug - Sat 24 Aug
⌄
Orlando - Chicago: Mon 19/08: £31
Chicago - Orlando: Sat 24/08: £30
Go
11 days
£61
Sat 10 Aug - Wed 21 Aug
⌄
Orlando - Chicago: Sat 10/08: £30
Chicago - Orlando: Wed 21/08: £31
Go
8 days
£61
Fri 16 Aug - Sat 24 Aug
⌄
Orlando - Chicago: Fri 16/08: £31
Chicago - Orlando: Sat 24/08: £30
Go
9 days
£61
Thu 15 Aug - Sat 24 Aug
⌄
Orlando - Chicago: Thu 15/08: £31
Chicago - Orlando: Sat 24/08: £30
Go
12 days
£61
Wed 14 Aug - Mon 26 Aug
⌄
Orlando - Chicago: Wed 14/08: £30
Chicago - Orlando: Mon 26/08: £31
Go
11 days
£61
Wed 14 Aug - Sun 25 Aug
⌄
Orlando - Chicago: Wed 14/08: £30
Chicago - Orlando: Sun 25/08: £31
Go
7 days
£61
Wed 14 Aug - Wed 21 Aug
⌄
Orlando - Chicago: Wed 14/08: £30
Chicago - Orlando: Wed 21/08: £31
Go
8 days
£61
Wed 14 Aug - Thu 22 Aug
⌄
Orlando - Chicago: Wed 14/08: £30
Chicago - Orlando: Thu 22/08: £31
Go
10 days
£61
Tue 13 Aug - Fri 23 Aug
⌄
Orlando - Chicago: Tue 13/08: £30
Chicago - Orlando: Fri 23/08: £31
Go
10 days
£61
Sat 10 Aug - Tue 20 Aug
⌄
Orlando - Chicago: Sat 10/08: £30
Chicago - Orlando: Tue 20/08: £31
Go
16 days
£61
Sat 10 Aug - Mon 26 Aug
⌄
Orlando - Chicago: Sat 10/08: £30
Chicago - Orlando: Mon 26/08: £31
Go
8 days
£61
Sat 10 Aug - Sun 18 Aug
⌄
Orlando - Chicago: Sat 10/08: £30
Chicago - Orlando: Sun 18/08: £31
Go
13 days
£61
Thu 8 Aug - Wed 21 Aug
⌄
Orlando - Chicago: Thu 8/08: £30
Chicago - Orlando: Wed 21/08: £31
Go
12 days
£61
Thu 8 Aug - Tue 20 Aug
⌄
Orlando - Chicago: Thu 8/08: £30
Chicago - Orlando: Tue 20/08: £31
Go
11 days
£61
Thu 8 Aug - Mon 19 Aug
⌄
Orlando - Chicago: Thu 8/08: £30
Chicago - Orlando: Mon 19/08: £31
Go
10 days
£61
Thu 8 Aug - Sun 18 Aug
⌄
Orlando - Chicago: Thu 8/08: £30
Chicago - Orlando: Sun 18/08: £31
Go
7 days
£61
Thu 8 Aug - Thu 15 Aug
⌄
Orlando - Chicago: Thu 8/08: £30
Chicago - Orlando: Thu 15/08: £31
Go
16 days
£61
Tue 6 Aug - Thu 22 Aug
⌄
Orlando - Chicago: Tue 6/08: £30
Chicago - Orlando: Thu 22/08: £31
Go
14 days
£61
Thu 8 Aug - Thu 22 Aug
⌄
Orlando - Chicago: Thu 8/08: £30
Chicago - Orlando: Thu 22/08: £31
Go
15 days
£61
Tue 6 Aug - Wed 21 Aug
⌄
Orlando - Chicago: Tue 6/08: £30
Chicago - Orlando: Wed 21/08: £31
Go
13 days
£61
Tue 6 Aug - Mon 19 Aug
⌄
Orlando - Chicago: Tue 6/08: £30
Chicago - Orlando: Mon 19/08: £31
Go
12 days
£61
Tue 6 Aug - Sun 18 Aug
⌄
Orlando - Chicago: Tue 6/08: £30
Chicago - Orlando: Sun 18/08: £31
Go
9 days
£61
Tue 6 Aug - Thu 15 Aug
⌄
Orlando - Chicago: Tue 6/08: £30
Chicago - Orlando: Thu 15/08: £31
Go
5 days
£61
Tue 6 Aug - Sun 11 Aug
⌄
Orlando - Chicago: Tue 6/08: £30
Chicago - Orlando: Sun 11/08: £31
Go
15 days
£61
Wed 24 Jul - Thu 8 Aug
⌄
Orlando - Chicago: Wed 24/07: £30
Chicago - Orlando: Thu 8/08: £31
Go
14 days
£61
Wed 24 Jul - Wed 7 Aug
⌄
Orlando - Chicago: Wed 24/07: £30
Chicago - Orlando: Wed 7/08: £31
Go
9 days
£61
Sat 10 Aug - Mon 19 Aug
⌄
Orlando - Chicago: Sat 10/08: £30
Chicago - Orlando: Mon 19/08: £31
Go
15 days
£61
Thu 8 Aug - Fri 23 Aug
⌄
Orlando - Chicago: Thu 8/08: £30
Chicago - Orlando: Fri 23/08: £31
Go
14 days
£61
Tue 6 Aug - Tue 20 Aug
⌄
Orlando - Chicago: Tue 6/08: £30
Chicago - Orlando: Tue 20/08: £31
Go
15 days
£61
Fri 9 Aug - Sat 24 Aug
⌄
Orlando - Chicago: Fri 9/08: £31
Chicago - Orlando: Sat 24/08: £30
Go
5 days
£61
Sat 10 Aug - Thu 15 Aug
⌄
Orlando - Chicago: Sat 10/08: £30
Chicago - Orlando: Thu 15/08: £31
Go
5 days
£62
Fri 16 Aug - Wed 21 Aug
⌄
Orlando - Chicago: Fri 16/08: £31
Chicago - Orlando: Wed 21/08: £31
Go
6 days
£62
Fri 16 Aug - Thu 22 Aug
⌄
Orlando - Chicago: Fri 16/08: £31
Chicago - Orlando: Thu 22/08: £31
Go
7 days
£62
Fri 16 Aug - Fri 23 Aug
⌄
Orlando - Chicago: Fri 16/08: £31
Chicago - Orlando: Fri 23/08: £31
Go
16 days
£62
Fri 9 Aug - Sun 25 Aug
⌄
Orlando - Chicago: Fri 9/08: £31
Chicago - Orlando: Sun 25/08: £31
Go
9 days
£62
Fri 16 Aug - Sun 25 Aug
⌄
Orlando - Chicago: Fri 16/08: £31
Chicago - Orlando: Sun 25/08: £31
Go
10 days
£62
Fri 16 Aug - Mon 26 Aug
⌄
Orlando - Chicago: Fri 16/08: £31
Chicago - Orlando: Mon 26/08: £31
Go
16 days
£62
Fri 16 Aug - Sun 1 Sep
⌄
Orlando - Chicago: Fri 16/08: £31
Chicago - Orlando: Sun 1/09: £31
Go
9 days
£62
Fri 9 Aug - Sun 18 Aug
⌄
Orlando - Chicago: Fri 9/08: £31
Chicago - Orlando: Sun 18/08: £31
Go
7 days
£62
Mon 19 Aug - Mon 26 Aug
⌄
Orlando - Chicago: Mon 19/08: £31
Chicago - Orlando: Mon 26/08: £31
Go
13 days
£62
Mon 19 Aug - Sun 1 Sep
⌄
Orlando - Chicago: Mon 19/08: £31
Chicago - Orlando: Sun 1/09: £31
Go
5 days
£62
Tue 20 Aug - Sun 25 Aug
⌄
Orlando - Chicago: Tue 20/08: £31
Chicago - Orlando: Sun 25/08: £31
Go
6 days
£62
Tue 20 Aug - Mon 26 Aug
⌄
Orlando - Chicago: Tue 20/08: £31
Chicago - Orlando: Mon 26/08: £31
Go
12 days
£62
Tue 20 Aug - Sun 1 Sep
⌄
Orlando - Chicago: Tue 20/08: £31
Chicago - Orlando: Sun 1/09: £31
Go
16 days
£62
Tue 20 Aug - Thu 5 Sep
⌄
Orlando - Chicago: Tue 20/08: £31
Chicago - Orlando: Thu 5/09: £31
Go
6 days
£62
Mon 26 Aug - Sun 1 Sep
⌄
Orlando - Chicago: Mon 26/08: £31
Chicago - Orlando: Sun 1/09: £31
Go
10 days
£62
Mon 26 Aug - Thu 5 Sep
⌄
Orlando - Chicago: Mon 26/08: £31
Chicago - Orlando: Thu 5/09: £31
Go
11 days
£62
Thu 15 Aug - Mon 26 Aug
⌄
Orlando - Chicago: Thu 15/08: £31
Chicago - Orlando: Mon 26/08: £31
Go
6 days
£62
Mon 19 Aug - Sun 25 Aug
⌄
Orlando - Chicago: Mon 19/08: £31
Chicago - Orlando: Sun 25/08: £31
Go
10 days
£62
Thu 15 Aug - Sun 25 Aug
⌄
Orlando - Chicago: Thu 15/08: £31
Chicago - Orlando: Sun 25/08: £31
Go
8 days
£62
Thu 15 Aug - Fri 23 Aug
⌄
Orlando - Chicago: Thu 15/08: £31
Chicago - Orlando: Fri 23/08: £31
Go
6 days
£62
Fri 9 Aug - Thu 15 Aug
⌄
Orlando - Chicago: Fri 9/08: £31
Chicago - Orlando: Thu 15/08: £31
Go
11 days
£62
Fri 9 Aug - Tue 20 Aug
⌄
Orlando - Chicago: Fri 9/08: £31
Chicago - Orlando: Tue 20/08: £31
Go
14 days
£62
Mon 12 Aug - Mon 26 Aug
⌄
Orlando - Chicago: Mon 12/08: £31
Chicago - Orlando: Mon 26/08: £31
Go
13 days
£62
Mon 12 Aug - Sun 25 Aug
⌄
Orlando - Chicago: Mon 12/08: £31
Chicago - Orlando: Sun 25/08: £31
Go
12 days
£62
Fri 9 Aug - Wed 21 Aug
⌄
Orlando - Chicago: Fri 9/08: £31
Chicago - Orlando: Wed 21/08: £31
Go
11 days
£62
Mon 12 Aug - Fri 23 Aug
⌄
Orlando - Chicago: Mon 12/08: £31
Chicago - Orlando: Fri 23/08: £31
Go
10 days
£62
Mon 12 Aug - Thu 22 Aug
⌄
Orlando - Chicago: Mon 12/08: £31
Chicago - Orlando: Thu 22/08: £31
Go
9 days
£62
Mon 12 Aug - Wed 21 Aug
⌄
Orlando - Chicago: Mon 12/08: £31
Chicago - Orlando: Wed 21/08: £31
Go
8 days
£62
Mon 12 Aug - Tue 20 Aug
⌄
Orlando - Chicago: Mon 12/08: £31
Chicago - Orlando: Tue 20/08: £31
Go
7 days
£62
Mon 12 Aug - Mon 19 Aug
⌄
Orlando - Chicago: Mon 12/08: £31
Chicago - Orlando: Mon 19/08: £31
Go
6 days
£62
Mon 12 Aug - Sun 18 Aug
⌄
Orlando - Chicago: Mon 12/08: £31
Chicago - Orlando: Sun 18/08: £31
Go
11 days
£62
Mon 26 Aug - Fri 6 Sep
⌄
Orlando - Chicago: Mon 26/08: £31
Chicago - Orlando: Fri 6/09: £31
Go
13 days
£62
Fri 9 Aug - Thu 22 Aug
⌄
Orlando - Chicago: Fri 9/08: £31
Chicago - Orlando: Thu 22/08: £31
Go
14 days
£62
Fri 9 Aug - Fri 23 Aug
⌄
Orlando - Chicago: Fri 9/08: £31
Chicago - Orlando: Fri 23/08: £31
Go
5 days
£62
Thu 15 Aug - Tue 20 Aug
⌄
Orlando - Chicago: Thu 15/08: £31
Chicago - Orlando: Tue 20/08: £31
Go
6 days
£62
Thu 15 Aug - Wed 21 Aug
⌄
Orlando - Chicago: Thu 15/08: £31
Chicago - Orlando: Wed 21/08: £31
Go
7 days
£62
Thu 15 Aug - Thu 22 Aug
⌄
Orlando - Chicago: Thu 15/08: £31
Chicago - Orlando: Thu 22/08: £31
Go
10 days
£62
Fri 9 Aug - Mon 19 Aug
⌄
Orlando - Chicago: Fri 9/08: £31
Chicago - Orlando: Mon 19/08: £31
Go
5 days
£62
Sun 1 Sep - Fri 6 Sep
⌄
Orlando - Chicago: Sun 1/09: £31
Chicago - Orlando: Fri 6/09: £31
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