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Chicago

from Orlando

Save up to: £148

Average cost: £210

Best deal: £62

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
£62
Tue 1 Sep - Tue 15 Sep
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Orlando - Chicago: Tue 1/09: £31
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Chicago - Orlando: Tue 15/09: £31
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15 days
£62
Tue 3 Nov - Wed 18 Nov
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Orlando - Chicago: Tue 3/11: £31
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Chicago - Orlando: Wed 18/11: £31
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14 days
£62
Tue 3 Nov - Tue 17 Nov
⌄
Orlando - Chicago: Tue 3/11: £31
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Chicago - Orlando: Tue 17/11: £31
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7 days
£62
Tue 3 Nov - Tue 10 Nov
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Orlando - Chicago: Tue 3/11: £31
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Chicago - Orlando: Tue 10/11: £31
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13 days
£62
Wed 28 Oct - Tue 10 Nov
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Orlando - Chicago: Wed 28/10: £31
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Chicago - Orlando: Tue 10/11: £31
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14 days
£62
Tue 27 Oct - Tue 10 Nov
⌄
Orlando - Chicago: Tue 27/10: £31
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Chicago - Orlando: Tue 10/11: £31
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6 days
£62
Wed 11 Nov - Tue 17 Nov
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Orlando - Chicago: Wed 11/11: £31
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Chicago - Orlando: Tue 17/11: £31
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15 days
£62
Tue 13 Oct - Wed 28 Oct
⌄
Orlando - Chicago: Tue 13/10: £31
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Chicago - Orlando: Wed 28/10: £31
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7 days
£62
Wed 21 Oct - Wed 28 Oct
⌄
Orlando - Chicago: Wed 21/10: £31
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Chicago - Orlando: Wed 28/10: £31
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13 days
£62
Wed 7 Oct - Tue 20 Oct
⌄
Orlando - Chicago: Wed 7/10: £31
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Chicago - Orlando: Tue 20/10: £31
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14 days
£62
Tue 6 Oct - Tue 20 Oct
⌄
Orlando - Chicago: Tue 6/10: £31
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Chicago - Orlando: Tue 20/10: £31
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7 days
£62
Tue 29 Sep - Tue 6 Oct
⌄
Orlando - Chicago: Tue 29/09: £31
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Chicago - Orlando: Tue 6/10: £31
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14 days
£62
Tue 22 Sep - Tue 6 Oct
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Orlando - Chicago: Tue 22/09: £31
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Chicago - Orlando: Tue 6/10: £31
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8 days
£62
Tue 22 Sep - Wed 30 Sep
⌄
Orlando - Chicago: Tue 22/09: £31
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Chicago - Orlando: Wed 30/09: £31
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7 days
£62
Tue 22 Sep - Tue 29 Sep
⌄
Orlando - Chicago: Tue 22/09: £31
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Chicago - Orlando: Tue 29/09: £31
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7 days
£62
Tue 13 Oct - Tue 20 Oct
⌄
Orlando - Chicago: Tue 13/10: £31
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Chicago - Orlando: Tue 20/10: £31
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7 days
£62
Wed 11 Nov - Wed 18 Nov
⌄
Orlando - Chicago: Wed 11/11: £31
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Chicago - Orlando: Wed 18/11: £31
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13 days
£69
Wed 21 Oct - Tue 3 Nov
⌄
Orlando - Chicago: Wed 21/10: £31
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Chicago - Orlando: Tue 3/11: £38
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7 days
£69
Tue 27 Oct - Tue 3 Nov
⌄
Orlando - Chicago: Tue 27/10: £31
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Chicago - Orlando: Tue 3/11: £38
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6 days
£69
Wed 28 Oct - Tue 3 Nov
⌄
Orlando - Chicago: Wed 28/10: £31
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Chicago - Orlando: Tue 3/11: £38
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