Chicago

from Dallas

Save up to: £185

Average cost: £225

Best deal: £40


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:

3 days
£40
Wed 26 Feb - Sat 1 Mar

Dallas - Chicago: Wed 26/02: £16
Chicago - Dallas: Sat 1/03: £24
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3 days
£48
Wed 2 Apr - Sat 5 Apr

Dallas - Chicago: Wed 2/04: £16
Chicago - Dallas: Sat 5/04: £32
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3 days
£48
Wed 9 Apr - Sat 12 Apr

Dallas - Chicago: Wed 9/04: £16
Chicago - Dallas: Sat 12/04: £32
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3 days
£48
Sat 22 Feb - Tue 25 Feb

Dallas - Chicago: Sat 22/02: £32
Chicago - Dallas: Tue 25/02: £16
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4 days
£48
Sat 22 Feb - Wed 26 Feb

Dallas - Chicago: Sat 22/02: £32
Chicago - Dallas: Wed 26/02: £16
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4 days
£48
Tue 8 Apr - Sat 12 Apr

Dallas - Chicago: Tue 8/04: £16
Chicago - Dallas: Sat 12/04: £32
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4 days
£48
Tue 1 Apr - Sat 5 Apr

Dallas - Chicago: Tue 1/04: £16
Chicago - Dallas: Sat 5/04: £32
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4 days
£48
Sat 1 Mar - Wed 5 Mar

Dallas - Chicago: Sat 1/03: £32
Chicago - Dallas: Wed 5/03: £16
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3 days
£48
Sat 1 Mar - Tue 4 Mar

Dallas - Chicago: Sat 1/03: £32
Chicago - Dallas: Tue 4/03: £16
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4 days
£48
Tue 25 Feb - Sat 1 Mar

Dallas - Chicago: Tue 25/02: £24
Chicago - Dallas: Sat 1/03: £24
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4 days
£52
Tue 15 Apr - Sat 19 Apr

Dallas - Chicago: Tue 15/04: £20
Chicago - Dallas: Sat 19/04: £32
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4 days
£52
Tue 22 Apr - Sat 26 Apr

Dallas - Chicago: Tue 22/04: £20
Chicago - Dallas: Sat 26/04: £32
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3 days
£52
Sat 26 Apr - Tue 29 Apr

Dallas - Chicago: Sat 26/04: £32
Chicago - Dallas: Tue 29/04: £20
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3 days
£52
Sat 19 Apr - Tue 22 Apr

Dallas - Chicago: Sat 19/04: £32
Chicago - Dallas: Tue 22/04: £20
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3 days
£55
Wed 28 May - Sat 31 May

Dallas - Chicago: Wed 28/05: £20
Chicago - Dallas: Sat 31/05: £35
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4 days
£55
Sat 31 May - Wed 4 Jun

Dallas - Chicago: Sat 31/05: £35
Chicago - Dallas: Wed 4/06: £20
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3 days
£55
Sat 10 May - Tue 13 May

Dallas - Chicago: Sat 10/05: £35
Chicago - Dallas: Tue 13/05: £20
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3 days
£55
Sat 3 May - Tue 6 May

Dallas - Chicago: Sat 3/05: £35
Chicago - Dallas: Tue 6/05: £20
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4 days
£55
Tue 6 May - Sat 10 May

Dallas - Chicago: Tue 6/05: £20
Chicago - Dallas: Sat 10/05: £35
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5 days
£56
Wed 9 Apr - Mon 14 Apr

Dallas - Chicago: Wed 9/04: £16
Chicago - Dallas: Mon 14/04: £40
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5 days
£59
Mon 5 May - Sat 10 May

Dallas - Chicago: Mon 5/05: £24
Chicago - Dallas: Sat 10/05: £35
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2 days
£59
Mon 5 May - Wed 7 May

Dallas - Chicago: Mon 5/05: £24
Chicago - Dallas: Wed 7/05: £35
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3 days
£64
Wed 16 Apr - Sat 19 Apr

Dallas - Chicago: Wed 16/04: £32
Chicago - Dallas: Sat 19/04: £32
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3 days
£64
Wed 12 Mar - Sat 15 Mar

Dallas - Chicago: Wed 12/03: £16
Chicago - Dallas: Sat 15/03: £48
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5 days
£64
Wed 19 Mar - Mon 24 Mar

Dallas - Chicago: Wed 19/03: £16
Chicago - Dallas: Mon 24/03: £48
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2 days
£64
Tue 25 Mar - Thu 27 Mar

Dallas - Chicago: Tue 25/03: £16
Chicago - Dallas: Thu 27/03: £48
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4 days
£64
Tue 25 Mar - Sat 29 Mar

Dallas - Chicago: Tue 25/03: £16
Chicago - Dallas: Sat 29/03: £48
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2 days
£64
Tue 1 Apr - Thu 3 Apr

Dallas - Chicago: Tue 1/04: £16
Chicago - Dallas: Thu 3/04: £48
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3 days
£64
Tue 1 Apr - Fri 4 Apr

Dallas - Chicago: Tue 1/04: £16
Chicago - Dallas: Fri 4/04: £48
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3 days
£64
Sun 23 Feb - Wed 26 Feb

Dallas - Chicago: Sun 23/02: £48
Chicago - Dallas: Wed 26/02: £16
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2 days
£64
Wed 2 Apr - Fri 4 Apr

Dallas - Chicago: Wed 2/04: £16
Chicago - Dallas: Fri 4/04: £48
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4 days
£64
Tue 11 Mar - Sat 15 Mar

Dallas - Chicago: Tue 11/03: £16
Chicago - Dallas: Sat 15/03: £48
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4 days
£64
Wed 2 Apr - Sun 6 Apr

Dallas - Chicago: Wed 2/04: £16
Chicago - Dallas: Sun 6/04: £48
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5 days
£64
Wed 2 Apr - Mon 7 Apr

Dallas - Chicago: Wed 2/04: £16
Chicago - Dallas: Mon 7/04: £48
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5 days
£64
Thu 3 Apr - Tue 8 Apr

Dallas - Chicago: Thu 3/04: £48
Chicago - Dallas: Tue 8/04: £16
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4 days
£64
Fri 4 Apr - Tue 8 Apr

Dallas - Chicago: Fri 4/04: £48
Chicago - Dallas: Tue 8/04: £16
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5 days
£64
Fri 4 Apr - Wed 9 Apr

Dallas - Chicago: Fri 4/04: £48
Chicago - Dallas: Wed 9/04: £16
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2 days
£64
Sun 23 Feb - Tue 25 Feb

Dallas - Chicago: Sun 23/02: £48
Chicago - Dallas: Tue 25/02: £16
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5 days
£64
Fri 21 Feb - Wed 26 Feb

Dallas - Chicago: Fri 21/02: £48
Chicago - Dallas: Wed 26/02: £16
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4 days
£64
Fri 21 Feb - Tue 25 Feb

Dallas - Chicago: Fri 21/02: £48
Chicago - Dallas: Tue 25/02: £16
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2 days
£64
Sat 26 Apr - Mon 28 Apr

Dallas - Chicago: Sat 26/04: £32
Chicago - Dallas: Mon 28/04: £32
Go

5 days
£64
Thu 20 Feb - Tue 25 Feb

Dallas - Chicago: Thu 20/02: £48
Chicago - Dallas: Tue 25/02: £16
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5 days
£64
Tue 1 Apr - Sun 6 Apr

Dallas - Chicago: Tue 1/04: £16
Chicago - Dallas: Sun 6/04: £48
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3 days
£64
Tue 11 Mar - Fri 14 Mar

Dallas - Chicago: Tue 11/03: £16
Chicago - Dallas: Fri 14/03: £48
Go

2 days
£64
Wed 12 Mar - Fri 14 Mar

Dallas - Chicago: Wed 12/03: £16
Chicago - Dallas: Fri 14/03: £48
Go

2 days
£64
Mon 10 Mar - Wed 12 Mar

Dallas - Chicago: Mon 10/03: £48
Chicago - Dallas: Wed 12/03: £16
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4 days
£64
Fri 28 Feb - Tue 4 Mar

Dallas - Chicago: Fri 28/02: £48
Chicago - Dallas: Tue 4/03: £16
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5 days
£64
Fri 28 Feb - Wed 5 Mar

Dallas - Chicago: Fri 28/02: £48
Chicago - Dallas: Wed 5/03: £16
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2 days
£64
Mon 24 Feb - Wed 26 Feb

Dallas - Chicago: Mon 24/02: £48
Chicago - Dallas: Wed 26/02: £16
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2 days
£64
Sun 2 Mar - Tue 4 Mar

Dallas - Chicago: Sun 2/03: £48
Chicago - Dallas: Tue 4/03: £16
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3 days
£64
Sun 2 Mar - Wed 5 Mar

Dallas - Chicago: Sun 2/03: £48
Chicago - Dallas: Wed 5/03: £16
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2 days
£64
Mon 3 Mar - Wed 5 Mar

Dallas - Chicago: Mon 3/03: £48
Chicago - Dallas: Wed 5/03: £16
Go

2 days
£64
Tue 11 Mar - Thu 13 Mar

Dallas - Chicago: Tue 11/03: £16
Chicago - Dallas: Thu 13/03: £48
Go

2 days
£64
Tue 4 Mar - Thu 6 Mar

Dallas - Chicago: Tue 4/03: £16
Chicago - Dallas: Thu 6/03: £48
Go

3 days
£64
Tue 4 Mar - Fri 7 Mar

Dallas - Chicago: Tue 4/03: £16
Chicago - Dallas: Fri 7/03: £48
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5 days
£64
Tue 4 Mar - Sun 9 Mar

Dallas - Chicago: Tue 4/03: £16
Chicago - Dallas: Sun 9/03: £48
Go

5 days
£64
Thu 27 Feb - Tue 4 Mar

Dallas - Chicago: Thu 27/02: £48
Chicago - Dallas: Tue 4/03: £16
Go

4 days
£64
Wed 5 Mar - Sun 9 Mar

Dallas - Chicago: Wed 5/03: £16
Chicago - Dallas: Sun 9/03: £48
Go

5 days
£64
Wed 5 Mar - Mon 10 Mar

Dallas - Chicago: Wed 5/03: £16
Chicago - Dallas: Mon 10/03: £48
Go

2 days
£64
Wed 5 Mar - Fri 7 Mar

Dallas - Chicago: Wed 5/03: £16
Chicago - Dallas: Fri 7/03: £48
Go

5 days
£64
Wed 26 Feb - Mon 3 Mar

Dallas - Chicago: Wed 26/02: £16
Chicago - Dallas: Mon 3/03: £48
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4 days
£64
Wed 26 Feb - Sun 2 Mar

Dallas - Chicago: Wed 26/02: £16
Chicago - Dallas: Sun 2/03: £48
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4 days
£64
Fri 7 Mar - Tue 11 Mar

Dallas - Chicago: Fri 7/03: £48
Chicago - Dallas: Tue 11/03: £16
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2 days
£64
Wed 26 Feb - Fri 28 Feb

Dallas - Chicago: Wed 26/02: £16
Chicago - Dallas: Fri 28/02: £48
Go

5 days
£64
Fri 7 Mar - Wed 12 Mar

Dallas - Chicago: Fri 7/03: £48
Chicago - Dallas: Wed 12/03: £16
Go

3 days
£64
Sat 8 Mar - Tue 11 Mar

Dallas - Chicago: Sat 8/03: £48
Chicago - Dallas: Tue 11/03: £16
Go

5 days
£64
Thu 6 Mar - Tue 11 Mar

Dallas - Chicago: Thu 6/03: £48
Chicago - Dallas: Tue 11/03: £16
Go

4 days
£64
Sat 8 Mar - Wed 12 Mar

Dallas - Chicago: Sat 8/03: £48
Chicago - Dallas: Wed 12/03: £16
Go

4 days
£65
Wed 9 Apr - Sun 13 Apr

Dallas - Chicago: Wed 9/04: £16
Chicago - Dallas: Sun 13/04: £49
Go

3 days
£65
Sun 9 Mar - Wed 12 Mar

Dallas - Chicago: Sun 9/03: £49
Chicago - Dallas: Wed 12/03: £16
Go

2 days
£65
Wed 9 Apr - Fri 11 Apr

Dallas - Chicago: Wed 9/04: £16
Chicago - Dallas: Fri 11/04: £49
Go

5 days
£65
Tue 8 Apr - Sun 13 Apr

Dallas - Chicago: Tue 8/04: £16
Chicago - Dallas: Sun 13/04: £49
Go

2 days
£65
Sun 9 Mar - Tue 11 Mar

Dallas - Chicago: Sun 9/03: £49
Chicago - Dallas: Tue 11/03: £16
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3 days
£65
Tue 8 Apr - Fri 11 Apr

Dallas - Chicago: Tue 8/04: £16
Chicago - Dallas: Fri 11/04: £49
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2 days
£65
Tue 8 Apr - Thu 10 Apr

Dallas - Chicago: Tue 8/04: £16
Chicago - Dallas: Thu 10/04: £49
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5 days
£65
Wed 12 Mar - Mon 17 Mar

Dallas - Chicago: Wed 12/03: £16
Chicago - Dallas: Mon 17/03: £49
Go

4 days
£65
Tue 4 Mar - Sat 8 Mar

Dallas - Chicago: Tue 4/03: £16
Chicago - Dallas: Sat 8/03: £49
Go

5 days
£65
Thu 27 Mar - Tue 1 Apr

Dallas - Chicago: Thu 27/03: £49
Chicago - Dallas: Tue 1/04: £16
Go

3 days
£65
Wed 5 Mar - Sat 8 Mar

Dallas - Chicago: Wed 5/03: £16
Chicago - Dallas: Sat 8/03: £49
Go

2 days
£65
Mon 7 Apr - Wed 9 Apr

Dallas - Chicago: Mon 7/04: £49
Chicago - Dallas: Wed 9/04: £16
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5 days
£67
Mon 28 Apr - Sat 3 May

Dallas - Chicago: Mon 28/04: £32
Chicago - Dallas: Sat 3/05: £35
Go

2 days
£68
Tue 22 Apr - Thu 24 Apr

Dallas - Chicago: Tue 22/04: £20
Chicago - Dallas: Thu 24/04: £48
Go

5 days
£68
Wed 28 May - Mon 2 Jun

Dallas - Chicago: Wed 28/05: £20
Chicago - Dallas: Mon 2/06: £48
Go

5 days
£68
Thu 24 Apr - Tue 29 Apr

Dallas - Chicago: Thu 24/04: £48
Chicago - Dallas: Tue 29/04: £20
Go

5 days
£68
Thu 1 May - Tue 6 May

Dallas - Chicago: Thu 1/05: £48
Chicago - Dallas: Tue 6/05: £20
Go

2 days
£68
Sun 4 May - Tue 6 May

Dallas - Chicago: Sun 4/05: £48
Chicago - Dallas: Tue 6/05: £20
Go

5 days
£68
Fri 30 May - Wed 4 Jun

Dallas - Chicago: Fri 30/05: £48
Chicago - Dallas: Wed 4/06: £20
Go

2 days
£68
Tue 6 May - Thu 8 May

Dallas - Chicago: Tue 6/05: £20
Chicago - Dallas: Thu 8/05: £48
Go

3 days
£68
Tue 6 May - Fri 9 May

Dallas - Chicago: Tue 6/05: £20
Chicago - Dallas: Fri 9/05: £48
Go

5 days
£68
Tue 6 May - Sun 11 May

Dallas - Chicago: Tue 6/05: £20
Chicago - Dallas: Sun 11/05: £48
Go

4 days
£68
Wed 28 May - Sun 1 Jun

Dallas - Chicago: Wed 28/05: £20
Chicago - Dallas: Sun 1/06: £48
Go

4 days
£68
Fri 9 May - Tue 13 May

Dallas - Chicago: Fri 9/05: £48
Chicago - Dallas: Tue 13/05: £20
Go

2 days
£68
Sun 11 May - Tue 13 May

Dallas - Chicago: Sun 11/05: £48
Chicago - Dallas: Tue 13/05: £20
Go

2 days
£68
Wed 28 May - Fri 30 May

Dallas - Chicago: Wed 28/05: £20
Chicago - Dallas: Fri 30/05: £48
Go

5 days
£68
Thu 8 May - Tue 13 May

Dallas - Chicago: Thu 8/05: £48
Chicago - Dallas: Tue 13/05: £20
Go

2 days
£68
Mon 2 Jun - Wed 4 Jun

Dallas - Chicago: Mon 2/06: £48
Chicago - Dallas: Wed 4/06: £20
Go

5 days
£68
Thu 17 Apr - Tue 22 Apr

Dallas - Chicago: Thu 17/04: £48
Chicago - Dallas: Tue 22/04: £20
Go

5 days
£68
Fri 21 Mar - Wed 26 Mar

Dallas - Chicago: Fri 21/03: £48
Chicago - Dallas: Wed 26/03: £20
Go

3 days
£68
Sat 22 Mar - Tue 25 Mar

Dallas - Chicago: Sat 22/03: £48
Chicago - Dallas: Tue 25/03: £20
Go

4 days
£68
Sat 22 Mar - Wed 26 Mar

Dallas - Chicago: Sat 22/03: £48
Chicago - Dallas: Wed 26/03: £20
Go

2 days
£68
Mon 24 Mar - Wed 26 Mar

Dallas - Chicago: Mon 24/03: £48
Chicago - Dallas: Wed 26/03: £20
Go

3 days
£68
Wed 26 Mar - Sat 29 Mar

Dallas - Chicago: Wed 26/03: £20
Chicago - Dallas: Sat 29/03: £48
Go

5 days
£68
Wed 26 Mar - Mon 31 Mar

Dallas - Chicago: Wed 26/03: £20
Chicago - Dallas: Mon 31/03: £48
Go

3 days
£68
Sun 1 Jun - Wed 4 Jun

Dallas - Chicago: Sun 1/06: £48
Chicago - Dallas: Wed 4/06: £20
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5 days
£68
Thu 10 Apr - Tue 15 Apr

Dallas - Chicago: Thu 10/04: £48
Chicago - Dallas: Tue 15/04: £20
Go

4 days
£68
Fri 21 Mar - Tue 25 Mar

Dallas - Chicago: Fri 21/03: £48
Chicago - Dallas: Tue 25/03: £20
Go

3 days
£68
Sat 12 Apr - Tue 15 Apr

Dallas - Chicago: Sat 12/04: £48
Chicago - Dallas: Tue 15/04: £20
Go

5 days
£68
Thu 20 Mar - Tue 25 Mar

Dallas - Chicago: Thu 20/03: £48
Chicago - Dallas: Tue 25/03: £20
Go

5 days
£68
Thu 13 Mar - Tue 18 Mar

Dallas - Chicago: Thu 13/03: £48
Chicago - Dallas: Tue 18/03: £20
Go

5 days
£68
Tue 15 Apr - Sun 20 Apr

Dallas - Chicago: Tue 15/04: £20
Chicago - Dallas: Sun 20/04: £48
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2 days
£68
Tue 15 Apr - Thu 17 Apr

Dallas - Chicago: Tue 15/04: £20
Chicago - Dallas: Thu 17/04: £48
Go

2 days
£69
Sun 20 Apr - Tue 22 Apr

Dallas - Chicago: Sun 20/04: £49
Chicago - Dallas: Tue 22/04: £20
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3 days
£69
Tue 13 May - Fri 16 May

Dallas - Chicago: Tue 13/05: £20
Chicago - Dallas: Fri 16/05: £49
Go

3 days
£69
Tue 22 Apr - Fri 25 Apr

Dallas - Chicago: Tue 22/04: £20
Chicago - Dallas: Fri 25/04: £49
Go

3 days
£69
Tue 15 Apr - Fri 18 Apr

Dallas - Chicago: Tue 15/04: £20
Chicago - Dallas: Fri 18/04: £49
Go

4 days
£69
Fri 18 Apr - Tue 22 Apr

Dallas - Chicago: Fri 18/04: £49
Chicago - Dallas: Tue 22/04: £20
Go

3 days
£69
Sat 15 Mar - Tue 18 Mar

Dallas - Chicago: Sat 15/03: £49
Chicago - Dallas: Tue 18/03: £20
Go

5 days
£69
Tue 22 Apr - Sun 27 Apr

Dallas - Chicago: Tue 22/04: £20
Chicago - Dallas: Sun 27/04: £49
Go

5 days
£69
Tue 13 May - Sun 18 May

Dallas - Chicago: Tue 13/05: £20
Chicago - Dallas: Sun 18/05: £49
Go

4 days
£69
Fri 25 Apr - Tue 29 Apr

Dallas - Chicago: Fri 25/04: £49
Chicago - Dallas: Tue 29/04: £20
Go

2 days
£69
Tue 13 May - Thu 15 May

Dallas - Chicago: Tue 13/05: £20
Chicago - Dallas: Thu 15/05: £49
Go

4 days
£69
Fri 11 Apr - Tue 15 Apr

Dallas - Chicago: Fri 11/04: £49
Chicago - Dallas: Tue 15/04: £20
Go

2 days
£69
Sun 27 Apr - Tue 29 Apr

Dallas - Chicago: Sun 27/04: £49
Chicago - Dallas: Tue 29/04: £20
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4 days
£69
Fri 2 May - Tue 6 May

Dallas - Chicago: Fri 2/05: £49
Chicago - Dallas: Tue 6/05: £20
Go

4 days
£70
Sat 10 May - Wed 14 May

Dallas - Chicago: Sat 10/05: £35
Chicago - Dallas: Wed 14/05: £35
Go

4 days
£70
Sat 3 May - Wed 7 May

Dallas - Chicago: Sat 3/05: £35
Chicago - Dallas: Wed 7/05: £35
Go

3 days
£70
Sat 31 May - Tue 3 Jun

Dallas - Chicago: Sat 31/05: £35
Chicago - Dallas: Tue 3/06: £35
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2 days
£71
Sat 3 May - Mon 5 May

Dallas - Chicago: Sat 3/05: £35
Chicago - Dallas: Mon 5/05: £36
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5 days
£72
Mon 24 Feb - Sat 1 Mar

Dallas - Chicago: Mon 24/02: £48
Chicago - Dallas: Sat 1/03: £24
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3 days
£72
Wed 19 Feb - Sat 22 Feb

Dallas - Chicago: Wed 19/02: £40
Chicago - Dallas: Sat 22/02: £32
Go

2 days
£72
Tue 25 Feb - Thu 27 Feb

Dallas - Chicago: Tue 25/02: £24
Chicago - Dallas: Thu 27/02: £48
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3 days
£72
Tue 25 Feb - Fri 28 Feb

Dallas - Chicago: Tue 25/02: £24
Chicago - Dallas: Fri 28/02: £48
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4 days
£72
Mon 5 May - Fri 9 May

Dallas - Chicago: Mon 5/05: £24
Chicago - Dallas: Fri 9/05: £48
Go

2 days
£72
Thu 27 Feb - Sat 1 Mar

Dallas - Chicago: Thu 27/02: £48
Chicago - Dallas: Sat 1/03: £24
Go

3 days
£72
Mon 5 May - Thu 8 May

Dallas - Chicago: Mon 5/05: £24
Chicago - Dallas: Thu 8/05: £48
Go

2 days
£72
Mon 14 Apr - Wed 16 Apr

Dallas - Chicago: Mon 14/04: £40
Chicago - Dallas: Wed 16/04: £32
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5 days
£72
Mon 14 Apr - Sat 19 Apr

Dallas - Chicago: Mon 14/04: £40
Chicago - Dallas: Sat 19/04: £32
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5 days
£72
Mon 21 Apr - Sat 26 Apr

Dallas - Chicago: Mon 21/04: £40
Chicago - Dallas: Sat 26/04: £32
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5 days
£72
Tue 25 Feb - Sun 2 Mar

Dallas - Chicago: Tue 25/02: £24
Chicago - Dallas: Sun 2/03: £48
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4 days
£72
Tue 18 Feb - Sat 22 Feb

Dallas - Chicago: Tue 18/02: £40
Chicago - Dallas: Sat 22/02: £32
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