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Chicago

from Dallas

Save up to: £135

Average cost: £193

Best deal: £58

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:

9 days
£58
Mon 4 Aug - Wed 13 Aug
⌄
Dallas - Chicago: Mon 4/08: £29
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Chicago - Dallas: Wed 13/08: £29
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10 days
£58
Mon 22 Sep - Thu 2 Oct
⌄
Dallas - Chicago: Mon 22/09: £29
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Chicago - Dallas: Thu 2/10: £29
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16 days
£58
Sat 20 Sep - Mon 6 Oct
⌄
Dallas - Chicago: Sat 20/09: £29
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Chicago - Dallas: Mon 6/10: £29
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14 days
£58
Sat 20 Sep - Sat 4 Oct
⌄
Dallas - Chicago: Sat 20/09: £29
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Chicago - Dallas: Sat 4/10: £29
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12 days
£58
Sat 20 Sep - Thu 2 Oct
⌄
Dallas - Chicago: Sat 20/09: £29
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Chicago - Dallas: Thu 2/10: £29
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5 days
£58
Sat 20 Sep - Thu 25 Sep
⌄
Dallas - Chicago: Sat 20/09: £29
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Chicago - Dallas: Thu 25/09: £29
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16 days
£58
Thu 18 Sep - Sat 4 Oct
⌄
Dallas - Chicago: Thu 18/09: £29
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Chicago - Dallas: Sat 4/10: £29
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14 days
£58
Thu 18 Sep - Thu 2 Oct
⌄
Dallas - Chicago: Thu 18/09: £29
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Chicago - Dallas: Thu 2/10: £29
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7 days
£58
Thu 18 Sep - Thu 25 Sep
⌄
Dallas - Chicago: Thu 18/09: £29
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Chicago - Dallas: Thu 25/09: £29
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15 days
£58
Wed 17 Sep - Thu 2 Oct
⌄
Dallas - Chicago: Wed 17/09: £29
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Chicago - Dallas: Thu 2/10: £29
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8 days
£58
Wed 17 Sep - Thu 25 Sep
⌄
Dallas - Chicago: Wed 17/09: £29
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Chicago - Dallas: Thu 25/09: £29
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16 days
£58
Tue 16 Sep - Thu 2 Oct
⌄
Dallas - Chicago: Tue 16/09: £29
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Chicago - Dallas: Thu 2/10: £29
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9 days
£58
Tue 16 Sep - Thu 25 Sep
⌄
Dallas - Chicago: Tue 16/09: £29
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Chicago - Dallas: Thu 25/09: £29
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10 days
£58
Mon 15 Sep - Thu 25 Sep
⌄
Dallas - Chicago: Mon 15/09: £29
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Chicago - Dallas: Thu 25/09: £29
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12 days
£58
Mon 22 Sep - Sat 4 Oct
⌄
Dallas - Chicago: Mon 22/09: £29
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Chicago - Dallas: Sat 4/10: £29
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5 days
£58
Mon 15 Sep - Sat 20 Sep
⌄
Dallas - Chicago: Mon 15/09: £29
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Chicago - Dallas: Sat 20/09: £29
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7 days
£58
Sat 13 Sep - Sat 20 Sep
⌄
Dallas - Chicago: Sat 13/09: £29
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Chicago - Dallas: Sat 20/09: £29
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5 days
£58
Sat 13 Sep - Thu 18 Sep
⌄
Dallas - Chicago: Sat 13/09: £29
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Chicago - Dallas: Thu 18/09: £29
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14 days
£58
Thu 11 Sep - Thu 25 Sep
⌄
Dallas - Chicago: Thu 11/09: £29
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Chicago - Dallas: Thu 25/09: £29
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9 days
£58
Thu 11 Sep - Sat 20 Sep
⌄
Dallas - Chicago: Thu 11/09: £29
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Chicago - Dallas: Sat 20/09: £29
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7 days
£58
Thu 11 Sep - Thu 18 Sep
⌄
Dallas - Chicago: Thu 11/09: £29
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Chicago - Dallas: Thu 18/09: £29
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16 days
£58
Tue 9 Sep - Thu 25 Sep
⌄
Dallas - Chicago: Tue 9/09: £29
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Chicago - Dallas: Thu 25/09: £29
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11 days
£58
Tue 9 Sep - Sat 20 Sep
⌄
Dallas - Chicago: Tue 9/09: £29
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Chicago - Dallas: Sat 20/09: £29
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9 days
£58
Tue 9 Sep - Thu 18 Sep
⌄
Dallas - Chicago: Tue 9/09: £29
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Chicago - Dallas: Thu 18/09: £29
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6 days
£58
Tue 9 Sep - Mon 15 Sep
⌄
Dallas - Chicago: Tue 9/09: £29
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Chicago - Dallas: Mon 15/09: £29
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12 days
£58
Mon 8 Sep - Sat 20 Sep
⌄
Dallas - Chicago: Mon 8/09: £29
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Chicago - Dallas: Sat 20/09: £29
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10 days
£58
Mon 8 Sep - Thu 18 Sep
⌄
Dallas - Chicago: Mon 8/09: £29
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Chicago - Dallas: Thu 18/09: £29
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7 days
£58
Mon 8 Sep - Mon 15 Sep
⌄
Dallas - Chicago: Mon 8/09: £29
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Chicago - Dallas: Mon 15/09: £29
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5 days
£58
Mon 8 Sep - Sat 13 Sep
⌄
Dallas - Chicago: Mon 8/09: £29
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Chicago - Dallas: Sat 13/09: £29
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12 days
£58
Sat 13 Sep - Thu 25 Sep
⌄
Dallas - Chicago: Sat 13/09: £29
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Chicago - Dallas: Thu 25/09: £29
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14 days
£58
Sat 6 Sep - Sat 20 Sep
⌄
Dallas - Chicago: Sat 6/09: £29
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Chicago - Dallas: Sat 20/09: £29
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14 days
£58
Mon 22 Sep - Mon 6 Oct
⌄
Dallas - Chicago: Mon 22/09: £29
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Chicago - Dallas: Mon 6/10: £29
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8 days
£58
Wed 24 Sep - Thu 2 Oct
⌄
Dallas - Chicago: Wed 24/09: £29
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Chicago - Dallas: Thu 2/10: £29
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9 days
£58
Mon 6 Oct - Wed 15 Oct
⌄
Dallas - Chicago: Mon 6/10: £29
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Chicago - Dallas: Wed 15/10: £29
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5 days
£58
Mon 6 Oct - Sat 11 Oct
⌄
Dallas - Chicago: Mon 6/10: £29
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Chicago - Dallas: Sat 11/10: £29
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14 days
£58
Wed 1 Oct - Wed 15 Oct
⌄
Dallas - Chicago: Wed 1/10: £29
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Chicago - Dallas: Wed 15/10: £29
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10 days
£58
Wed 1 Oct - Sat 11 Oct
⌄
Dallas - Chicago: Wed 1/10: £29
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Chicago - Dallas: Sat 11/10: £29
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8 days
£58
Wed 1 Oct - Thu 9 Oct
⌄
Dallas - Chicago: Wed 1/10: £29
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Chicago - Dallas: Thu 9/10: £29
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6 days
£58
Wed 1 Oct - Tue 7 Oct
⌄
Dallas - Chicago: Wed 1/10: £29
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Chicago - Dallas: Tue 7/10: £29
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5 days
£58
Wed 1 Oct - Mon 6 Oct
⌄
Dallas - Chicago: Wed 1/10: £29
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Chicago - Dallas: Mon 6/10: £29
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15 days
£58
Tue 30 Sep - Wed 15 Oct
⌄
Dallas - Chicago: Tue 30/09: £29
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Chicago - Dallas: Wed 15/10: £29
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11 days
£58
Tue 30 Sep - Sat 11 Oct
⌄
Dallas - Chicago: Tue 30/09: £29
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Chicago - Dallas: Sat 11/10: £29
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9 days
£58
Tue 30 Sep - Thu 9 Oct
⌄
Dallas - Chicago: Tue 30/09: £29
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Chicago - Dallas: Thu 9/10: £29
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7 days
£58
Tue 30 Sep - Tue 7 Oct
⌄
Dallas - Chicago: Tue 30/09: £29
Go
Chicago - Dallas: Tue 7/10: £29
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6 days
£58
Tue 30 Sep - Mon 6 Oct
⌄
Dallas - Chicago: Tue 30/09: £29
Go
Chicago - Dallas: Mon 6/10: £29
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16 days
£58
Mon 29 Sep - Wed 15 Oct
⌄
Dallas - Chicago: Mon 29/09: £29
Go
Chicago - Dallas: Wed 15/10: £29
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15 days
£58
Mon 22 Sep - Tue 7 Oct
⌄
Dallas - Chicago: Mon 22/09: £29
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Chicago - Dallas: Tue 7/10: £29
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12 days
£58
Mon 29 Sep - Sat 11 Oct
⌄
Dallas - Chicago: Mon 29/09: £29
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Chicago - Dallas: Sat 11/10: £29
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8 days
£58
Mon 29 Sep - Tue 7 Oct
⌄
Dallas - Chicago: Mon 29/09: £29
Go
Chicago - Dallas: Tue 7/10: £29
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7 days
£58
Mon 29 Sep - Mon 6 Oct
⌄
Dallas - Chicago: Mon 29/09: £29
Go
Chicago - Dallas: Mon 6/10: £29
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5 days
£58
Mon 29 Sep - Sat 4 Oct
⌄
Dallas - Chicago: Mon 29/09: £29
Go
Chicago - Dallas: Sat 4/10: £29
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14 days
£58
Sat 27 Sep - Sat 11 Oct
⌄
Dallas - Chicago: Sat 27/09: £29
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Chicago - Dallas: Sat 11/10: £29
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12 days
£58
Sat 27 Sep - Thu 9 Oct
⌄
Dallas - Chicago: Sat 27/09: £29
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Chicago - Dallas: Thu 9/10: £29
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10 days
£58
Sat 27 Sep - Tue 7 Oct
⌄
Dallas - Chicago: Sat 27/09: £29
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Chicago - Dallas: Tue 7/10: £29
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9 days
£58
Sat 27 Sep - Mon 6 Oct
⌄
Dallas - Chicago: Sat 27/09: £29
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Chicago - Dallas: Mon 6/10: £29
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7 days
£58
Sat 27 Sep - Sat 4 Oct
⌄
Dallas - Chicago: Sat 27/09: £29
Go
Chicago - Dallas: Sat 4/10: £29
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5 days
£58
Sat 27 Sep - Thu 2 Oct
⌄
Dallas - Chicago: Sat 27/09: £29
Go
Chicago - Dallas: Thu 2/10: £29
Go
15 days
£58
Wed 24 Sep - Thu 9 Oct
⌄
Dallas - Chicago: Wed 24/09: £29
Go
Chicago - Dallas: Thu 9/10: £29
Go
13 days
£58
Wed 24 Sep - Tue 7 Oct
⌄
Dallas - Chicago: Wed 24/09: £29
Go
Chicago - Dallas: Tue 7/10: £29
Go
12 days
£58
Wed 24 Sep - Mon 6 Oct
⌄
Dallas - Chicago: Wed 24/09: £29
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Chicago - Dallas: Mon 6/10: £29
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10 days
£58
Wed 24 Sep - Sat 4 Oct
⌄
Dallas - Chicago: Wed 24/09: £29
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Chicago - Dallas: Sat 4/10: £29
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10 days
£58
Mon 29 Sep - Thu 9 Oct
⌄
Dallas - Chicago: Mon 29/09: £29
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Chicago - Dallas: Thu 9/10: £29
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12 days
£58
Sat 6 Sep - Thu 18 Sep
⌄
Dallas - Chicago: Sat 6/09: £29
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Chicago - Dallas: Thu 18/09: £29
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9 days
£58
Sat 6 Sep - Mon 15 Sep
⌄
Dallas - Chicago: Sat 6/09: £29
Go
Chicago - Dallas: Mon 15/09: £29
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7 days
£58
Sat 6 Sep - Sat 13 Sep
⌄
Dallas - Chicago: Sat 6/09: £29
Go
Chicago - Dallas: Sat 13/09: £29
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8 days
£58
Tue 7 Oct - Wed 15 Oct
⌄
Dallas - Chicago: Tue 7/10: £29
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Chicago - Dallas: Wed 15/10: £29
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14 days
£58
Wed 13 Aug - Wed 27 Aug
⌄
Dallas - Chicago: Wed 13/08: £29
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Chicago - Dallas: Wed 27/08: £29
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13 days
£58
Wed 13 Aug - Tue 26 Aug
⌄
Dallas - Chicago: Wed 13/08: £29
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Chicago - Dallas: Tue 26/08: £29
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12 days
£58
Wed 13 Aug - Mon 25 Aug
⌄
Dallas - Chicago: Wed 13/08: £29
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Chicago - Dallas: Mon 25/08: £29
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8 days
£58
Wed 13 Aug - Thu 21 Aug
⌄
Dallas - Chicago: Wed 13/08: £29
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Chicago - Dallas: Thu 21/08: £29
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6 days
£58
Wed 13 Aug - Tue 19 Aug
⌄
Dallas - Chicago: Wed 13/08: £29
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Chicago - Dallas: Tue 19/08: £29
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16 days
£58
Tue 12 Aug - Thu 28 Aug
⌄
Dallas - Chicago: Tue 12/08: £29
Go
Chicago - Dallas: Thu 28/08: £29
Go
15 days
£58
Tue 12 Aug - Wed 27 Aug
⌄
Dallas - Chicago: Tue 12/08: £29
Go
Chicago - Dallas: Wed 27/08: £29
Go
14 days
£58
Tue 12 Aug - Tue 26 Aug
⌄
Dallas - Chicago: Tue 12/08: £29
Go
Chicago - Dallas: Tue 26/08: £29
Go
13 days
£58
Tue 12 Aug - Mon 25 Aug
⌄
Dallas - Chicago: Tue 12/08: £29
Go
Chicago - Dallas: Mon 25/08: £29
Go
9 days
£58
Tue 12 Aug - Thu 21 Aug
⌄
Dallas - Chicago: Tue 12/08: £29
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Chicago - Dallas: Thu 21/08: £29
Go
7 days
£58
Tue 12 Aug - Tue 19 Aug
⌄
Dallas - Chicago: Tue 12/08: £29
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Chicago - Dallas: Tue 19/08: £29
Go
15 days
£58
Wed 6 Aug - Thu 21 Aug
⌄
Dallas - Chicago: Wed 6/08: £29
Go
Chicago - Dallas: Thu 21/08: £29
Go
13 days
£58
Wed 6 Aug - Tue 19 Aug
⌄
Dallas - Chicago: Wed 6/08: £29
Go
Chicago - Dallas: Tue 19/08: £29
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10 days
£58
Wed 6 Aug - Sat 16 Aug
⌄
Dallas - Chicago: Wed 6/08: £29
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Chicago - Dallas: Sat 16/08: £29
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8 days
£58
Wed 6 Aug - Thu 14 Aug
⌄
Dallas - Chicago: Wed 6/08: £29
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Chicago - Dallas: Thu 14/08: £29
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7 days
£58
Wed 6 Aug - Wed 13 Aug
⌄
Dallas - Chicago: Wed 6/08: £29
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Chicago - Dallas: Wed 13/08: £29
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16 days
£58
Tue 5 Aug - Thu 21 Aug
⌄
Dallas - Chicago: Tue 5/08: £29
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Chicago - Dallas: Thu 21/08: £29
Go
14 days
£58
Tue 5 Aug - Tue 19 Aug
⌄
Dallas - Chicago: Tue 5/08: £29
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Chicago - Dallas: Tue 19/08: £29
Go
11 days
£58
Tue 5 Aug - Sat 16 Aug
⌄
Dallas - Chicago: Tue 5/08: £29
Go
Chicago - Dallas: Sat 16/08: £29
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9 days
£58
Tue 5 Aug - Thu 14 Aug
⌄
Dallas - Chicago: Tue 5/08: £29
Go
Chicago - Dallas: Thu 14/08: £29
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8 days
£58
Tue 5 Aug - Wed 13 Aug
⌄
Dallas - Chicago: Tue 5/08: £29
Go
Chicago - Dallas: Wed 13/08: £29
Go
15 days
£58
Mon 4 Aug - Tue 19 Aug
⌄
Dallas - Chicago: Mon 4/08: £29
Go
Chicago - Dallas: Tue 19/08: £29
Go
12 days
£58
Mon 4 Aug - Sat 16 Aug
⌄
Dallas - Chicago: Mon 4/08: £29
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Chicago - Dallas: Sat 16/08: £29
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10 days
£58
Mon 4 Aug - Thu 14 Aug
⌄
Dallas - Chicago: Mon 4/08: £29
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Chicago - Dallas: Thu 14/08: £29
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5 days
£58
Thu 21 Aug - Tue 26 Aug
⌄
Dallas - Chicago: Thu 21/08: £29
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Chicago - Dallas: Tue 26/08: £29
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6 days
£58
Thu 21 Aug - Wed 27 Aug
⌄
Dallas - Chicago: Thu 21/08: £29
Go
Chicago - Dallas: Wed 27/08: £29
Go
15 days
£58
Wed 13 Aug - Thu 28 Aug
⌄
Dallas - Chicago: Wed 13/08: £29
Go
Chicago - Dallas: Thu 28/08: £29
Go
9 days
£58
Thu 21 Aug - Sat 30 Aug
⌄
Dallas - Chicago: Thu 21/08: £29
Go
Chicago - Dallas: Sat 30/08: £29
Go
5 days
£58
Sat 6 Sep - Thu 11 Sep
⌄
Dallas - Chicago: Sat 6/09: £29
Go
Chicago - Dallas: Thu 11/09: £29
Go
16 days
£58
Thu 4 Sep - Sat 20 Sep
⌄
Dallas - Chicago: Thu 4/09: £29
Go
Chicago - Dallas: Sat 20/09: £29
Go
14 days
£58
Thu 4 Sep - Thu 18 Sep
⌄
Dallas - Chicago: Thu 4/09: £29
Go
Chicago - Dallas: Thu 18/09: £29
Go
11 days
£58
Thu 4 Sep - Mon 15 Sep
⌄
Dallas - Chicago: Thu 4/09: £29
Go
Chicago - Dallas: Mon 15/09: £29
Go
9 days
£58
Thu 4 Sep - Sat 13 Sep
⌄
Dallas - Chicago: Thu 4/09: £29
Go
Chicago - Dallas: Sat 13/09: £29
Go
7 days
£58
Thu 4 Sep - Thu 11 Sep
⌄
Dallas - Chicago: Thu 4/09: £29
Go
Chicago - Dallas: Thu 11/09: £29
Go
15 days
£58
Wed 3 Sep - Thu 18 Sep
⌄
Dallas - Chicago: Wed 3/09: £29
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Chicago - Dallas: Thu 18/09: £29
Go
12 days
£58
Wed 3 Sep - Mon 15 Sep
⌄
Dallas - Chicago: Wed 3/09: £29
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Chicago - Dallas: Mon 15/09: £29
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10 days
£58
Wed 3 Sep - Sat 13 Sep
⌄
Dallas - Chicago: Wed 3/09: £29
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Chicago - Dallas: Sat 13/09: £29
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8 days
£58
Wed 3 Sep - Thu 11 Sep
⌄
Dallas - Chicago: Wed 3/09: £29
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Chicago - Dallas: Thu 11/09: £29
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5 days
£58
Wed 3 Sep - Mon 8 Sep
⌄
Dallas - Chicago: Wed 3/09: £29
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Chicago - Dallas: Mon 8/09: £29
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14 days
£58
Mon 1 Sep - Mon 15 Sep
⌄
Dallas - Chicago: Mon 1/09: £29
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Chicago - Dallas: Mon 15/09: £29
Go
12 days
£58
Mon 1 Sep - Sat 13 Sep
⌄
Dallas - Chicago: Mon 1/09: £29
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Chicago - Dallas: Sat 13/09: £29
Go
7 days
£58
Thu 21 Aug - Thu 28 Aug
⌄
Dallas - Chicago: Thu 21/08: £29
Go
Chicago - Dallas: Thu 28/08: £29
Go
7 days
£58
Wed 8 Oct - Wed 15 Oct
⌄
Dallas - Chicago: Wed 8/10: £29
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Chicago - Dallas: Wed 15/10: £29
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11 days
£58
Tue 26 Aug - Sat 6 Sep
⌄
Dallas - Chicago: Tue 26/08: £29
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Chicago - Dallas: Sat 6/09: £29
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14 days
£58
Thu 21 Aug - Thu 4 Sep
⌄
Dallas - Chicago: Thu 21/08: £29
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Chicago - Dallas: Thu 4/09: £29
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16 days
£58
Thu 21 Aug - Sat 6 Sep
⌄
Dallas - Chicago: Thu 21/08: £29
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Chicago - Dallas: Sat 6/09: £29
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5 days
£58
Mon 25 Aug - Sat 30 Aug
⌄
Dallas - Chicago: Mon 25/08: £29
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Chicago - Dallas: Sat 30/08: £29
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10 days
£58
Mon 1 Sep - Thu 11 Sep
⌄
Dallas - Chicago: Mon 1/09: £29
Go
Chicago - Dallas: Thu 11/09: £29
Go
7 days
£58
Mon 1 Sep - Mon 8 Sep
⌄
Dallas - Chicago: Mon 1/09: £29
Go
Chicago - Dallas: Mon 8/09: £29
Go
5 days
£58
Mon 1 Sep - Sat 6 Sep
⌄
Dallas - Chicago: Mon 1/09: £29
Go
Chicago - Dallas: Sat 6/09: £29
Go
16 days
£58
Tue 26 Aug - Thu 11 Sep
⌄
Dallas - Chicago: Tue 26/08: £29
Go
Chicago - Dallas: Thu 11/09: £29
Go
13 days
£58
Tue 26 Aug - Mon 8 Sep
⌄
Dallas - Chicago: Tue 26/08: £29
Go
Chicago - Dallas: Mon 8/09: £29
Go
10 days
£58
Mon 25 Aug - Thu 4 Sep
⌄
Dallas - Chicago: Mon 25/08: £29
Go
Chicago - Dallas: Thu 4/09: £29
Go
9 days
£58
Tue 26 Aug - Thu 4 Sep
⌄
Dallas - Chicago: Tue 26/08: £29
Go
Chicago - Dallas: Thu 4/09: £29
Go
14 days
£58
Mon 25 Aug - Mon 8 Sep
⌄
Dallas - Chicago: Mon 25/08: £29
Go
Chicago - Dallas: Mon 8/09: £29
Go
12 days
£58
Mon 25 Aug - Sat 6 Sep
⌄
Dallas - Chicago: Mon 25/08: £29
Go
Chicago - Dallas: Sat 6/09: £29
Go
14 days
£59
Mon 11 Aug - Mon 25 Aug
⌄
Dallas - Chicago: Mon 11/08: £30
Go
Chicago - Dallas: Mon 25/08: £29
Go
5 days
£59
Mon 11 Aug - Sat 16 Aug
⌄
Dallas - Chicago: Mon 11/08: £30
Go
Chicago - Dallas: Sat 16/08: £29
Go
8 days
£59
Mon 11 Aug - Tue 19 Aug
⌄
Dallas - Chicago: Mon 11/08: £30
Go
Chicago - Dallas: Tue 19/08: £29
Go
16 days
£59
Mon 11 Aug - Wed 27 Aug
⌄
Dallas - Chicago: Mon 11/08: £30
Go
Chicago - Dallas: Wed 27/08: £29
Go
15 days
£59
Mon 11 Aug - Tue 26 Aug
⌄
Dallas - Chicago: Mon 11/08: £30
Go
Chicago - Dallas: Tue 26/08: £29
Go
10 days
£59
Mon 11 Aug - Thu 21 Aug
⌄
Dallas - Chicago: Mon 11/08: £30
Go
Chicago - Dallas: Thu 21/08: £29
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