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Chicago

from Orlando

Save up to: £207

Average cost: £249

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:

14 days
£42
Tue 11 Aug - Tue 25 Aug
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Orlando - Chicago: Tue 11/08: £21
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Chicago - Orlando: Tue 25/08: £21
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8 days
£42
Tue 15 Sep - Wed 23 Sep
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Orlando - Chicago: Tue 15/09: £21
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Chicago - Orlando: Wed 23/09: £21
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7 days
£42
Tue 15 Sep - Tue 22 Sep
⌄
Orlando - Chicago: Tue 15/09: £21
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Chicago - Orlando: Tue 22/09: £21
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14 days
£42
Wed 9 Sep - Wed 23 Sep
⌄
Orlando - Chicago: Wed 9/09: £21
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Chicago - Orlando: Wed 23/09: £21
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13 days
£42
Wed 9 Sep - Tue 22 Sep
⌄
Orlando - Chicago: Wed 9/09: £21
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Chicago - Orlando: Tue 22/09: £21
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7 days
£42
Wed 9 Sep - Wed 16 Sep
⌄
Orlando - Chicago: Wed 9/09: £21
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Chicago - Orlando: Wed 16/09: £21
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6 days
£42
Wed 9 Sep - Tue 15 Sep
⌄
Orlando - Chicago: Wed 9/09: £21
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Chicago - Orlando: Tue 15/09: £21
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6 days
£42
Wed 16 Sep - Tue 22 Sep
⌄
Orlando - Chicago: Wed 16/09: £21
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Chicago - Orlando: Tue 22/09: £21
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7 days
£42
Wed 16 Sep - Wed 23 Sep
⌄
Orlando - Chicago: Wed 16/09: £21
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Chicago - Orlando: Wed 23/09: £21
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9 days
£54
Sun 24 May - Tue 2 Jun
⌄
Orlando - Chicago: Sun 24/05: £33
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Chicago - Orlando: Tue 2/06: £21
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10 days
£54
Sun 24 May - Wed 3 Jun
⌄
Orlando - Chicago: Sun 24/05: £33
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Chicago - Orlando: Wed 3/06: £21
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16 days
£54
Sun 24 May - Tue 9 Jun
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Orlando - Chicago: Sun 24/05: £33
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Chicago - Orlando: Tue 9/06: £21
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8 days
£59
Sun 24 May - Mon 1 Jun
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Orlando - Chicago: Sun 24/05: £33
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Chicago - Orlando: Mon 1/06: £26
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11 days
£59
Sun 24 May - Thu 4 Jun
⌄
Orlando - Chicago: Sun 24/05: £33
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Chicago - Orlando: Thu 4/06: £26
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7 days
£75
Tue 26 May - Tue 2 Jun
⌄
Orlando - Chicago: Tue 26/05: £54
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Chicago - Orlando: Tue 2/06: £21
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15 days
£75
Tue 8 Sep - Wed 23 Sep
⌄
Orlando - Chicago: Tue 8/09: £54
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Chicago - Orlando: Wed 23/09: £21
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14 days
£75
Tue 8 Sep - Tue 22 Sep
⌄
Orlando - Chicago: Tue 8/09: £54
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Chicago - Orlando: Tue 22/09: £21
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8 days
£75
Tue 8 Sep - Wed 16 Sep
⌄
Orlando - Chicago: Tue 8/09: £54
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Chicago - Orlando: Wed 16/09: £21
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7 days
£75
Tue 8 Sep - Tue 15 Sep
⌄
Orlando - Chicago: Tue 8/09: £54
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Chicago - Orlando: Tue 15/09: £21
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13 days
£75
Wed 2 Sep - Tue 15 Sep
⌄
Orlando - Chicago: Wed 2/09: £54
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Chicago - Orlando: Tue 15/09: £21
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14 days
£75
Tue 26 May - Tue 9 Jun
⌄
Orlando - Chicago: Tue 26/05: £54
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Chicago - Orlando: Tue 9/06: £21
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15 days
£75
Tue 25 Aug - Wed 9 Sep
⌄
Orlando - Chicago: Tue 25/08: £54
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Chicago - Orlando: Wed 9/09: £21
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15 days
£75
Tue 11 Aug - Wed 26 Aug
⌄
Orlando - Chicago: Tue 11/08: £21
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Chicago - Orlando: Wed 26/08: £54
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8 days
£75
Tue 26 May - Wed 3 Jun
⌄
Orlando - Chicago: Tue 26/05: £54
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Chicago - Orlando: Wed 3/06: £21
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8 days
£75
Tue 11 Aug - Wed 19 Aug
⌄
Orlando - Chicago: Tue 11/08: £21
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Chicago - Orlando: Wed 19/08: £54
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13 days
£75
Wed 27 May - Tue 9 Jun
⌄
Orlando - Chicago: Wed 27/05: £54
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Chicago - Orlando: Tue 9/06: £21
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7 days
£75
Wed 27 May - Wed 3 Jun
⌄
Orlando - Chicago: Wed 27/05: £54
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Chicago - Orlando: Wed 3/06: £21
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6 days
£75
Wed 27 May - Tue 2 Jun
⌄
Orlando - Chicago: Wed 27/05: £54
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Chicago - Orlando: Tue 2/06: £21
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7 days
£75
Wed 2 Sep - Wed 9 Sep
⌄
Orlando - Chicago: Wed 2/09: £54
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Chicago - Orlando: Wed 9/09: £21
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14 days
£75
Wed 2 Sep - Wed 16 Sep
⌄
Orlando - Chicago: Wed 2/09: £54
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Chicago - Orlando: Wed 16/09: £21
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9 days
£80
Tue 26 May - Thu 4 Jun
⌄
Orlando - Chicago: Tue 26/05: £54
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Chicago - Orlando: Thu 4/06: £26
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6 days
£80
Tue 26 May - Mon 1 Jun
⌄
Orlando - Chicago: Tue 26/05: £54
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Chicago - Orlando: Mon 1/06: £26
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8 days
£80
Wed 27 May - Thu 4 Jun
⌄
Orlando - Chicago: Wed 27/05: £54
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Chicago - Orlando: Thu 4/06: £26
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5 days
£80
Wed 27 May - Mon 1 Jun
⌄
Orlando - Chicago: Wed 27/05: £54
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Chicago - Orlando: Mon 1/06: £26
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