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Chicago

from Houston

Save up to: £141

Average cost: £203

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:

11 days
£62
Thu 9 Oct - Mon 20 Oct
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Houston - Chicago: Thu 9/10: £31
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Chicago - Houston: Mon 20/10: £31
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10 days
£62
Thu 30 Oct - Sun 9 Nov
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Houston - Chicago: Thu 30/10: £31
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Chicago - Houston: Sun 9/11: £31
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7 days
£62
Mon 8 Dec - Mon 15 Dec
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Houston - Chicago: Mon 8/12: £31
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Chicago - Houston: Mon 15/12: £31
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14 days
£62
Thu 30 Oct - Thu 13 Nov
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Houston - Chicago: Thu 30/10: £31
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Chicago - Houston: Thu 13/11: £31
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16 days
£62
Thu 30 Oct - Sat 15 Nov
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Houston - Chicago: Thu 30/10: £31
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Chicago - Houston: Sat 15/11: £31
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6 days
£62
Mon 8 Dec - Sun 14 Dec
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Houston - Chicago: Mon 8/12: £31
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Chicago - Houston: Sun 14/12: £31
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6 days
£62
Fri 31 Oct - Thu 6 Nov
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Houston - Chicago: Fri 31/10: £31
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Chicago - Houston: Thu 6/11: £31
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9 days
£62
Fri 31 Oct - Sun 9 Nov
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Houston - Chicago: Fri 31/10: £31
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Chicago - Houston: Sun 9/11: £31
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13 days
£62
Fri 31 Oct - Thu 13 Nov
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Houston - Chicago: Fri 31/10: £31
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Chicago - Houston: Thu 13/11: £31
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15 days
£62
Fri 31 Oct - Sat 15 Nov
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Houston - Chicago: Fri 31/10: £31
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Chicago - Houston: Sat 15/11: £31
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5 days
£62
Sat 1 Nov - Thu 6 Nov
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Houston - Chicago: Sat 1/11: £31
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Chicago - Houston: Thu 6/11: £31
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7 days
£62
Sat 1 Nov - Sat 8 Nov
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Houston - Chicago: Sat 1/11: £31
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Chicago - Houston: Sat 8/11: £31
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8 days
£62
Sat 1 Nov - Sun 9 Nov
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Houston - Chicago: Sat 1/11: £31
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Chicago - Houston: Sun 9/11: £31
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8 days
£62
Sun 7 Dec - Mon 15 Dec
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Houston - Chicago: Sun 7/12: £31
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Chicago - Houston: Mon 15/12: £31
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12 days
£62
Sat 1 Nov - Thu 13 Nov
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Houston - Chicago: Sat 1/11: £31
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Chicago - Houston: Thu 13/11: £31
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14 days
£62
Sat 1 Nov - Sat 15 Nov
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Houston - Chicago: Sat 1/11: £31
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Chicago - Houston: Sat 15/11: £31
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16 days
£62
Sat 1 Nov - Mon 17 Nov
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Houston - Chicago: Sat 1/11: £31
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Chicago - Houston: Mon 17/11: £31
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7 days
£62
Sun 7 Dec - Sun 14 Dec
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Houston - Chicago: Sun 7/12: £31
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Chicago - Houston: Sun 14/12: £31
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5 days
£62
Sun 7 Dec - Fri 12 Dec
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Houston - Chicago: Sun 7/12: £31
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Chicago - Houston: Fri 12/12: £31
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7 days
£62
Thu 6 Nov - Thu 13 Nov
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Houston - Chicago: Thu 6/11: £31
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Chicago - Houston: Thu 13/11: £31
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9 days
£62
Thu 6 Nov - Sat 15 Nov
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Houston - Chicago: Thu 6/11: £31
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Chicago - Houston: Sat 15/11: £31
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11 days
£62
Thu 6 Nov - Mon 17 Nov
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Houston - Chicago: Thu 6/11: £31
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Chicago - Houston: Mon 17/11: £31
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14 days
£62
Thu 6 Nov - Thu 20 Nov
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Houston - Chicago: Thu 6/11: £31
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Chicago - Houston: Thu 20/11: £31
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10 days
£62
Fri 5 Dec - Mon 15 Dec
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Houston - Chicago: Fri 5/12: £31
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Chicago - Houston: Mon 15/12: £31
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9 days
£62
Fri 5 Dec - Sun 14 Dec
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Houston - Chicago: Fri 5/12: £31
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Chicago - Houston: Sun 14/12: £31
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7 days
£62
Fri 5 Dec - Fri 12 Dec
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Houston - Chicago: Fri 5/12: £31
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Chicago - Houston: Fri 12/12: £31
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7 days
£62
Thu 13 Nov - Thu 20 Nov
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Houston - Chicago: Thu 13/11: £31
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Chicago - Houston: Thu 20/11: £31
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5 days
£62
Sat 15 Nov - Thu 20 Nov
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Houston - Chicago: Sat 15/11: £31
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Chicago - Houston: Thu 20/11: £31
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9 days
£62
Thu 30 Oct - Sat 8 Nov
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Houston - Chicago: Thu 30/10: £31
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Chicago - Houston: Sat 8/11: £31
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7 days
£62
Thu 30 Oct - Thu 6 Nov
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Houston - Chicago: Thu 30/10: £31
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Chicago - Houston: Thu 6/11: £31
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8 days
£62
Fri 31 Oct - Sat 8 Nov
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Houston - Chicago: Fri 31/10: £31
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Chicago - Houston: Sat 8/11: £31
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15 days
£62
Sat 25 Oct - Sun 9 Nov
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Houston - Chicago: Sat 25/10: £31
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Chicago - Houston: Sun 9/11: £31
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14 days
£62
Thu 9 Oct - Thu 23 Oct
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Houston - Chicago: Thu 9/10: £31
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Chicago - Houston: Thu 23/10: £31
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16 days
£62
Thu 9 Oct - Sat 25 Oct
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Houston - Chicago: Thu 9/10: £31
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Chicago - Houston: Sat 25/10: £31
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9 days
£62
Sat 11 Oct - Mon 20 Oct
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Houston - Chicago: Sat 11/10: £31
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Chicago - Houston: Mon 20/10: £31
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12 days
£62
Sat 11 Oct - Thu 23 Oct
⌄
Houston - Chicago: Sat 11/10: £31
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Chicago - Houston: Thu 23/10: £31
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14 days
£62
Sat 11 Oct - Sat 25 Oct
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Houston - Chicago: Sat 11/10: £31
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Chicago - Houston: Sat 25/10: £31
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16 days
£62
Sat 11 Oct - Mon 27 Oct
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Houston - Chicago: Sat 11/10: £31
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Chicago - Houston: Mon 27/10: £31
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5 days
£62
Sat 18 Oct - Thu 23 Oct
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Houston - Chicago: Sat 18/10: £31
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Chicago - Houston: Thu 23/10: £31
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7 days
£62
Sat 18 Oct - Sat 25 Oct
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Houston - Chicago: Sat 18/10: £31
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Chicago - Houston: Sat 25/10: £31
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9 days
£62
Sat 18 Oct - Mon 27 Oct
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Houston - Chicago: Sat 18/10: £31
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Chicago - Houston: Mon 27/10: £31
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14 days
£62
Sat 18 Oct - Sat 1 Nov
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Houston - Chicago: Sat 18/10: £31
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Chicago - Houston: Sat 1/11: £31
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15 days
£62
Sat 18 Oct - Sun 2 Nov
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Houston - Chicago: Sat 18/10: £31
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Chicago - Houston: Sun 2/11: £31
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16 days
£62
Sat 18 Oct - Mon 3 Nov
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Houston - Chicago: Sat 18/10: £31
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Chicago - Houston: Mon 3/11: £31
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7 days
£62
Thu 23 Oct - Thu 30 Oct
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Houston - Chicago: Thu 23/10: £31
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Chicago - Houston: Thu 30/10: £31
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9 days
£62
Thu 23 Oct - Sat 1 Nov
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Houston - Chicago: Thu 23/10: £31
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Chicago - Houston: Sat 1/11: £31
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10 days
£62
Thu 23 Oct - Sun 2 Nov
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Houston - Chicago: Thu 23/10: £31
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Chicago - Houston: Sun 2/11: £31
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12 days
£62
Sat 18 Oct - Thu 30 Oct
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Houston - Chicago: Sat 18/10: £31
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Chicago - Houston: Thu 30/10: £31
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8 days
£62
Sat 25 Oct - Sun 2 Nov
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Houston - Chicago: Sat 25/10: £31
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Chicago - Houston: Sun 2/11: £31
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14 days
£62
Thu 23 Oct - Thu 6 Nov
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Houston - Chicago: Thu 23/10: £31
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Chicago - Houston: Thu 6/11: £31
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16 days
£62
Thu 23 Oct - Sat 8 Nov
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Houston - Chicago: Thu 23/10: £31
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Chicago - Houston: Sat 8/11: £31
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14 days
£62
Sat 25 Oct - Sat 8 Nov
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Houston - Chicago: Sat 25/10: £31
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Chicago - Houston: Sat 8/11: £31
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11 days
£62
Thu 23 Oct - Mon 3 Nov
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Houston - Chicago: Thu 23/10: £31
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Chicago - Houston: Mon 3/11: £31
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12 days
£62
Sat 25 Oct - Thu 6 Nov
⌄
Houston - Chicago: Sat 25/10: £31
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Chicago - Houston: Thu 6/11: £31
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7 days
£62
Sat 25 Oct - Sat 1 Nov
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Houston - Chicago: Sat 25/10: £31
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Chicago - Houston: Sat 1/11: £31
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9 days
£62
Sat 25 Oct - Mon 3 Nov
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Houston - Chicago: Sat 25/10: £31
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Chicago - Houston: Mon 3/11: £31
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5 days
£62
Sat 25 Oct - Thu 30 Oct
⌄
Houston - Chicago: Sat 25/10: £31
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Chicago - Houston: Thu 30/10: £31
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9 days
£65
Sun 7 Dec - Tue 16 Dec
⌄
Houston - Chicago: Sun 7/12: £31
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Chicago - Houston: Tue 16/12: £34
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5 days
£65
Fri 5 Dec - Wed 10 Dec
⌄
Houston - Chicago: Fri 5/12: £31
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Chicago - Houston: Wed 10/12: £34
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11 days
£65
Wed 3 Dec - Sun 14 Dec
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Houston - Chicago: Wed 3/12: £34
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Chicago - Houston: Sun 14/12: £31
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9 days
£65
Wed 3 Dec - Fri 12 Dec
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Houston - Chicago: Wed 3/12: £34
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Chicago - Houston: Fri 12/12: £31
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5 days
£65
Wed 3 Dec - Mon 8 Dec
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Houston - Chicago: Wed 3/12: £34
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Chicago - Houston: Mon 8/12: £31
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13 days
£65
Tue 2 Dec - Mon 15 Dec
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Houston - Chicago: Tue 2/12: £34
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Chicago - Houston: Mon 15/12: £31
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8 days
£65
Mon 8 Dec - Tue 16 Dec
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Houston - Chicago: Mon 8/12: £31
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Chicago - Houston: Tue 16/12: £34
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12 days
£65
Tue 2 Dec - Sun 14 Dec
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Houston - Chicago: Tue 2/12: £34
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Chicago - Houston: Sun 14/12: £31
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12 days
£65
Wed 3 Dec - Mon 15 Dec
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Houston - Chicago: Wed 3/12: £34
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Chicago - Houston: Mon 15/12: £31
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8 days
£65
Fri 5 Dec - Sat 13 Dec
⌄
Houston - Chicago: Fri 5/12: £31
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Chicago - Houston: Sat 13/12: £34
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11 days
£65
Fri 5 Dec - Tue 16 Dec
⌄
Houston - Chicago: Fri 5/12: £31
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Chicago - Houston: Tue 16/12: £34
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12 days
£65
Fri 5 Dec - Wed 17 Dec
⌄
Houston - Chicago: Fri 5/12: £31
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Chicago - Houston: Wed 17/12: £34
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10 days
£65
Tue 2 Dec - Fri 12 Dec
⌄
Houston - Chicago: Tue 2/12: £34
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Chicago - Houston: Fri 12/12: £31
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6 days
£65
Sat 6 Dec - Fri 12 Dec
⌄
Houston - Chicago: Sat 6/12: £34
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Chicago - Houston: Fri 12/12: £31
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8 days
£65
Sat 6 Dec - Sun 14 Dec
⌄
Houston - Chicago: Sat 6/12: £34
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Chicago - Houston: Sun 14/12: £31
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9 days
£65
Sat 6 Dec - Mon 15 Dec
⌄
Houston - Chicago: Sat 6/12: £34
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Chicago - Houston: Mon 15/12: £31
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9 days
£65
Mon 8 Dec - Wed 17 Dec
⌄
Houston - Chicago: Mon 8/12: £31
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Chicago - Houston: Wed 17/12: £34
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6 days
£65
Sun 7 Dec - Sat 13 Dec
⌄
Houston - Chicago: Sun 7/12: £31
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Chicago - Houston: Sat 13/12: £34
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5 days
£65
Mon 8 Dec - Sat 13 Dec
⌄
Houston - Chicago: Mon 8/12: £31
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Chicago - Houston: Sat 13/12: £34
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10 days
£65
Sun 7 Dec - Wed 17 Dec
⌄
Houston - Chicago: Sun 7/12: £31
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Chicago - Houston: Wed 17/12: £34
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6 days
£65
Tue 9 Dec - Mon 15 Dec
⌄
Houston - Chicago: Tue 9/12: £34
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Chicago - Houston: Mon 15/12: £31
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5 days
£65
Tue 9 Dec - Sun 14 Dec
⌄
Houston - Chicago: Tue 9/12: £34
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Chicago - Houston: Sun 14/12: £31
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6 days
£65
Tue 2 Dec - Mon 8 Dec
⌄
Houston - Chicago: Tue 2/12: £34
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Chicago - Houston: Mon 8/12: £31
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15 days
£65
Wed 5 Nov - Thu 20 Nov
⌄
Houston - Chicago: Wed 5/11: £34
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Chicago - Houston: Thu 20/11: £31
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16 days
£65
Thu 20 Nov - Sat 6 Dec
⌄
Houston - Chicago: Thu 20/11: £31
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Chicago - Houston: Sat 6/12: £34
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13 days
£65
Thu 23 Oct - Wed 5 Nov
⌄
Houston - Chicago: Thu 23/10: £31
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Chicago - Houston: Wed 5/11: £34
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11 days
£65
Sat 25 Oct - Wed 5 Nov
⌄
Houston - Chicago: Sat 25/10: £31
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Chicago - Houston: Wed 5/11: £34
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6 days
£65
Thu 30 Oct - Wed 5 Nov
⌄
Houston - Chicago: Thu 30/10: £31
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Chicago - Houston: Wed 5/11: £34
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12 days
£65
Thu 30 Oct - Tue 11 Nov
⌄
Houston - Chicago: Thu 30/10: £31
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Chicago - Houston: Tue 11/11: £34
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13 days
£65
Thu 30 Oct - Wed 12 Nov
⌄
Houston - Chicago: Thu 30/10: £31
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Chicago - Houston: Wed 12/11: £34
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5 days
£65
Fri 31 Oct - Wed 5 Nov
⌄
Houston - Chicago: Fri 31/10: £31
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Chicago - Houston: Wed 5/11: £34
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11 days
£65
Fri 31 Oct - Tue 11 Nov
⌄
Houston - Chicago: Fri 31/10: £31
Go
Chicago - Houston: Tue 11/11: £34
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12 days
£65
Fri 31 Oct - Wed 12 Nov
⌄
Houston - Chicago: Fri 31/10: £31
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Chicago - Houston: Wed 12/11: £34
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10 days
£65
Sat 1 Nov - Tue 11 Nov
⌄
Houston - Chicago: Sat 1/11: £31
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Chicago - Houston: Tue 11/11: £34
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11 days
£65
Sat 1 Nov - Wed 12 Nov
⌄
Houston - Chicago: Sat 1/11: £31
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Chicago - Houston: Wed 12/11: £34
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8 days
£65
Wed 5 Nov - Thu 13 Nov
⌄
Houston - Chicago: Wed 5/11: £34
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Chicago - Houston: Thu 13/11: £31
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10 days
£65
Wed 5 Nov - Sat 15 Nov
⌄
Houston - Chicago: Wed 5/11: £34
Go
Chicago - Houston: Sat 15/11: £31
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12 days
£65
Wed 5 Nov - Mon 17 Nov
⌄
Houston - Chicago: Wed 5/11: £34
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Chicago - Houston: Mon 17/11: £31
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5 days
£65
Wed 10 Dec - Mon 15 Dec
⌄
Houston - Chicago: Wed 10/12: £34
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Chicago - Houston: Mon 15/12: £31
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5 days
£65
Thu 6 Nov - Tue 11 Nov
⌄
Houston - Chicago: Thu 6/11: £31
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Chicago - Houston: Tue 11/11: £34
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6 days
£65
Thu 6 Nov - Wed 12 Nov
⌄
Houston - Chicago: Thu 6/11: £31
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Chicago - Houston: Wed 12/11: £34
Go
12 days
£65
Thu 6 Nov - Tue 18 Nov
⌄
Houston - Chicago: Thu 6/11: £31
Go
Chicago - Houston: Tue 18/11: £34
Go
13 days
£65
Thu 6 Nov - Wed 19 Nov
⌄
Houston - Chicago: Thu 6/11: £31
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Chicago - Houston: Wed 19/11: £34
Go
5 days
£65
Sat 8 Nov - Thu 13 Nov
⌄
Houston - Chicago: Sat 8/11: £34
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Chicago - Houston: Thu 13/11: £31
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7 days
£65
Sat 8 Nov - Sat 15 Nov
⌄
Houston - Chicago: Sat 8/11: £34
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Chicago - Houston: Sat 15/11: £31
Go
9 days
£65
Sat 8 Nov - Mon 17 Nov
⌄
Houston - Chicago: Sat 8/11: £34
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Chicago - Houston: Mon 17/11: £31
Go
12 days
£65
Sat 8 Nov - Thu 20 Nov
⌄
Houston - Chicago: Sat 8/11: £34
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Chicago - Houston: Thu 20/11: £31
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6 days
£65
Tue 11 Nov - Mon 17 Nov
⌄
Houston - Chicago: Tue 11/11: £34
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Chicago - Houston: Mon 17/11: £31
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9 days
£65
Tue 11 Nov - Thu 20 Nov
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Houston - Chicago: Tue 11/11: £34
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Chicago - Houston: Thu 20/11: £31
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5 days
£65
Wed 12 Nov - Mon 17 Nov
⌄
Houston - Chicago: Wed 12/11: £34
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Chicago - Houston: Mon 17/11: £31
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8 days
£65
Wed 12 Nov - Thu 20 Nov
⌄
Houston - Chicago: Wed 12/11: £34
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Chicago - Houston: Thu 20/11: £31
Go
5 days
£65
Thu 13 Nov - Tue 18 Nov
⌄
Houston - Chicago: Thu 13/11: £31
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Chicago - Houston: Tue 18/11: £34
Go
6 days
£65
Thu 13 Nov - Wed 19 Nov
⌄
Houston - Chicago: Thu 13/11: £31
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Chicago - Houston: Wed 19/11: £34
Go
13 days
£65
Thu 20 Nov - Wed 3 Dec
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Houston - Chicago: Thu 20/11: £31
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Chicago - Houston: Wed 3/12: £34
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5 days
£65
Tue 2 Dec - Sun 7 Dec
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Houston - Chicago: Tue 2/12: £34
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Chicago - Houston: Sun 7/12: £31
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5 days
£65
Fri 12 Dec - Wed 17 Dec
⌄
Houston - Chicago: Fri 12/12: £31
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Chicago - Houston: Wed 17/12: £34
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