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Chicago

from Houston

Save up to: £118

Average cost: £164

Best deal: £46

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:

8 days
£46
Thu 12 Feb - Fri 20 Feb
⌄
Houston - Chicago: Thu 12/02: £23
Go
Chicago - Houston: Fri 20/02: £23
Go
7 days
£46
Sun 18 Jan - Sun 25 Jan
⌄
Houston - Chicago: Sun 18/01: £23
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Chicago - Houston: Sun 25/01: £23
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9 days
£46
Fri 30 Jan - Sun 8 Feb
⌄
Houston - Chicago: Fri 30/01: £23
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Chicago - Houston: Sun 8/02: £23
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7 days
£46
Sun 25 Jan - Sun 1 Feb
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Houston - Chicago: Sun 25/01: £23
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Chicago - Houston: Sun 1/02: £23
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5 days
£46
Sun 1 Feb - Fri 6 Feb
⌄
Houston - Chicago: Sun 1/02: £23
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Chicago - Houston: Fri 6/02: £23
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7 days
£46
Sun 1 Feb - Sun 8 Feb
⌄
Houston - Chicago: Sun 1/02: £23
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Chicago - Houston: Sun 8/02: £23
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14 days
£46
Sun 18 Jan - Sun 1 Feb
⌄
Houston - Chicago: Sun 18/01: £23
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Chicago - Houston: Sun 1/02: £23
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14 days
£46
Sun 11 Jan - Sun 25 Jan
⌄
Houston - Chicago: Sun 11/01: £23
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Chicago - Houston: Sun 25/01: £23
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12 days
£46
Sun 11 Jan - Fri 23 Jan
⌄
Houston - Chicago: Sun 11/01: £23
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Chicago - Houston: Fri 23/01: £23
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5 days
£46
Sun 18 Jan - Fri 23 Jan
⌄
Houston - Chicago: Sun 18/01: £23
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Chicago - Houston: Fri 23/01: £23
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7 days
£46
Sun 11 Jan - Sun 18 Jan
⌄
Houston - Chicago: Sun 11/01: £23
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Chicago - Houston: Sun 18/01: £23
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14 days
£46
Sun 25 Jan - Sun 8 Feb
⌄
Houston - Chicago: Sun 25/01: £23
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Chicago - Houston: Sun 8/02: £23
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8 days
£46
Sun 11 Jan - Mon 19 Jan
⌄
Houston - Chicago: Sun 11/01: £23
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Chicago - Houston: Mon 19/01: £23
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14 days
£46
Fri 6 Feb - Fri 20 Feb
⌄
Houston - Chicago: Fri 6/02: £23
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Chicago - Houston: Fri 20/02: £23
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16 days
£46
Fri 23 Jan - Sun 8 Feb
⌄
Houston - Chicago: Fri 23/01: £23
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Chicago - Houston: Sun 8/02: £23
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7 days
£46
Thu 12 Feb - Thu 19 Feb
⌄
Houston - Chicago: Thu 12/02: £23
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Chicago - Houston: Thu 19/02: £23
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14 days
£46
Fri 23 Jan - Fri 6 Feb
⌄
Houston - Chicago: Fri 23/01: £23
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Chicago - Houston: Fri 6/02: £23
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13 days
£46
Fri 6 Feb - Thu 19 Feb
⌄
Houston - Chicago: Fri 6/02: £23
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Chicago - Houston: Thu 19/02: £23
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12 days
£46
Sun 25 Jan - Fri 6 Feb
⌄
Houston - Chicago: Sun 25/01: £23
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Chicago - Houston: Fri 6/02: £23
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7 days
£46
Fri 30 Jan - Fri 6 Feb
⌄
Houston - Chicago: Fri 30/01: £23
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Chicago - Houston: Fri 6/02: £23
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9 days
£46
Fri 23 Jan - Sun 1 Feb
⌄
Houston - Chicago: Fri 23/01: £23
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Chicago - Houston: Sun 1/02: £23
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13 days
£51
Mon 26 Jan - Sun 8 Feb
⌄
Houston - Chicago: Mon 26/01: £28
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Chicago - Houston: Sun 8/02: £23
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8 days
£51
Sun 25 Jan - Mon 2 Feb
⌄
Houston - Chicago: Sun 25/01: £23
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Chicago - Houston: Mon 2/02: £28
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15 days
£51
Sun 25 Jan - Mon 9 Feb
⌄
Houston - Chicago: Sun 25/01: £23
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Chicago - Houston: Mon 9/02: £28
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6 days
£51
Fri 30 Jan - Thu 5 Feb
⌄
Houston - Chicago: Fri 30/01: £23
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Chicago - Houston: Thu 5/02: £28
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16 days
£51
Sun 25 Jan - Tue 10 Feb
⌄
Houston - Chicago: Sun 25/01: £23
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Chicago - Houston: Tue 10/02: £28
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5 days
£51
Fri 30 Jan - Wed 4 Feb
⌄
Houston - Chicago: Fri 30/01: £23
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Chicago - Houston: Wed 4/02: £28
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10 days
£51
Thu 29 Jan - Sun 8 Feb
⌄
Houston - Chicago: Thu 29/01: £28
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Chicago - Houston: Sun 8/02: £23
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8 days
£51
Thu 29 Jan - Fri 6 Feb
⌄
Houston - Chicago: Thu 29/01: £28
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Chicago - Houston: Fri 6/02: £23
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6 days
£51
Mon 26 Jan - Sun 1 Feb
⌄
Houston - Chicago: Mon 26/01: £28
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Chicago - Houston: Sun 1/02: £23
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11 days
£51
Wed 28 Jan - Sun 8 Feb
⌄
Houston - Chicago: Wed 28/01: £28
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Chicago - Houston: Sun 8/02: £23
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9 days
£51
Wed 28 Jan - Fri 6 Feb
⌄
Houston - Chicago: Wed 28/01: £28
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Chicago - Houston: Fri 6/02: £23
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11 days
£51
Mon 26 Jan - Fri 6 Feb
⌄
Houston - Chicago: Mon 26/01: £28
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Chicago - Houston: Fri 6/02: £23
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12 days
£51
Tue 27 Jan - Sun 8 Feb
⌄
Houston - Chicago: Tue 27/01: £28
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Chicago - Houston: Sun 8/02: £23
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11 days
£51
Sun 25 Jan - Thu 5 Feb
⌄
Houston - Chicago: Sun 25/01: £23
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Chicago - Houston: Thu 5/02: £28
Go
10 days
£51
Tue 27 Jan - Fri 6 Feb
⌄
Houston - Chicago: Tue 27/01: £28
Go
Chicago - Houston: Fri 6/02: £23
Go
13 days
£51
Sun 25 Jan - Sat 7 Feb
⌄
Houston - Chicago: Sun 25/01: £23
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Chicago - Houston: Sat 7/02: £28
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5 days
£51
Tue 27 Jan - Sun 1 Feb
⌄
Houston - Chicago: Tue 27/01: £28
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Chicago - Houston: Sun 1/02: £23
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9 days
£51
Sun 25 Jan - Tue 3 Feb
⌄
Houston - Chicago: Sun 25/01: £23
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Chicago - Houston: Tue 3/02: £28
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10 days
£51
Sun 25 Jan - Wed 4 Feb
⌄
Houston - Chicago: Sun 25/01: £23
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Chicago - Houston: Wed 4/02: £28
Go
11 days
£51
Fri 30 Jan - Tue 10 Feb
⌄
Houston - Chicago: Fri 30/01: £23
Go
Chicago - Houston: Tue 10/02: £28
Go
10 days
£51
Fri 30 Jan - Mon 9 Feb
⌄
Houston - Chicago: Fri 30/01: £23
Go
Chicago - Houston: Mon 9/02: £28
Go
9 days
£51
Wed 11 Feb - Fri 20 Feb
⌄
Houston - Chicago: Wed 11/02: £28
Go
Chicago - Houston: Fri 20/02: £23
Go
8 days
£51
Wed 11 Feb - Thu 19 Feb
⌄
Houston - Chicago: Wed 11/02: £28
Go
Chicago - Houston: Thu 19/02: £23
Go
10 days
£51
Tue 10 Feb - Fri 20 Feb
⌄
Houston - Chicago: Tue 10/02: £28
Go
Chicago - Houston: Fri 20/02: £23
Go
9 days
£51
Tue 10 Feb - Thu 19 Feb
⌄
Houston - Chicago: Tue 10/02: £28
Go
Chicago - Houston: Thu 19/02: £23
Go
11 days
£51
Mon 9 Feb - Fri 20 Feb
⌄
Houston - Chicago: Mon 9/02: £28
Go
Chicago - Houston: Fri 20/02: £23
Go
10 days
£51
Mon 9 Feb - Thu 19 Feb
⌄
Houston - Chicago: Mon 9/02: £28
Go
Chicago - Houston: Thu 19/02: £23
Go
12 days
£51
Sun 8 Feb - Fri 20 Feb
⌄
Houston - Chicago: Sun 8/02: £28
Go
Chicago - Houston: Fri 20/02: £23
Go
11 days
£51
Sun 8 Feb - Thu 19 Feb
⌄
Houston - Chicago: Sun 8/02: £28
Go
Chicago - Houston: Thu 19/02: £23
Go
13 days
£51
Sat 7 Feb - Fri 20 Feb
⌄
Houston - Chicago: Sat 7/02: £28
Go
Chicago - Houston: Fri 20/02: £23
Go
12 days
£51
Sat 7 Feb - Thu 19 Feb
⌄
Houston - Chicago: Sat 7/02: £28
Go
Chicago - Houston: Thu 19/02: £23
Go
5 days
£51
Fri 6 Feb - Wed 11 Feb
⌄
Houston - Chicago: Fri 6/02: £23
Go
Chicago - Houston: Wed 11/02: £28
Go
15 days
£51
Thu 5 Feb - Fri 20 Feb
⌄
Houston - Chicago: Thu 5/02: £28
Go
Chicago - Houston: Fri 20/02: £23
Go
14 days
£51
Thu 5 Feb - Thu 19 Feb
⌄
Houston - Chicago: Thu 5/02: £28
Go
Chicago - Houston: Thu 19/02: £23
Go
16 days
£51
Wed 4 Feb - Fri 20 Feb
⌄
Houston - Chicago: Wed 4/02: £28
Go
Chicago - Houston: Fri 20/02: £23
Go
15 days
£51
Wed 4 Feb - Thu 19 Feb
⌄
Houston - Chicago: Wed 4/02: £28
Go
Chicago - Houston: Thu 19/02: £23
Go
16 days
£51
Tue 3 Feb - Thu 19 Feb
⌄
Houston - Chicago: Tue 3/02: £28
Go
Chicago - Houston: Thu 19/02: £23
Go
5 days
£51
Tue 3 Feb - Sun 8 Feb
⌄
Houston - Chicago: Tue 3/02: £28
Go
Chicago - Houston: Sun 8/02: £23
Go
6 days
£51
Mon 2 Feb - Sun 8 Feb
⌄
Houston - Chicago: Mon 2/02: £28
Go
Chicago - Houston: Sun 8/02: £23
Go
10 days
£51
Sun 1 Feb - Wed 11 Feb
⌄
Houston - Chicago: Sun 1/02: £23
Go
Chicago - Houston: Wed 11/02: £28
Go
9 days
£51
Sun 1 Feb - Tue 10 Feb
⌄
Houston - Chicago: Sun 1/02: £23
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Chicago - Houston: Tue 10/02: £28
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8 days
£51
Sun 1 Feb - Mon 9 Feb
⌄
Houston - Chicago: Sun 1/02: £23
Go
Chicago - Houston: Mon 9/02: £28
Go
6 days
£51
Sun 1 Feb - Sat 7 Feb
⌄
Houston - Chicago: Sun 1/02: £23
Go
Chicago - Houston: Sat 7/02: £28
Go
8 days
£51
Sat 31 Jan - Sun 8 Feb
⌄
Houston - Chicago: Sat 31/01: £28
Go
Chicago - Houston: Sun 8/02: £23
Go
6 days
£51
Sat 31 Jan - Fri 6 Feb
⌄
Houston - Chicago: Sat 31/01: £28
Go
Chicago - Houston: Fri 6/02: £23
Go
12 days
£51
Fri 30 Jan - Wed 11 Feb
⌄
Houston - Chicago: Fri 30/01: £23
Go
Chicago - Houston: Wed 11/02: £28
Go
8 days
£51
Fri 30 Jan - Sat 7 Feb
⌄
Houston - Chicago: Fri 30/01: £23
Go
Chicago - Houston: Sat 7/02: £28
Go
6 days
£51
Sun 25 Jan - Sat 31 Jan
⌄
Houston - Chicago: Sun 25/01: £23
Go
Chicago - Houston: Sat 31/01: £28
Go
15 days
£51
Fri 23 Jan - Sat 7 Feb
⌄
Houston - Chicago: Fri 23/01: £23
Go
Chicago - Houston: Sat 7/02: £28
Go
15 days
£51
Sat 24 Jan - Sun 8 Feb
⌄
Houston - Chicago: Sat 24/01: £28
Go
Chicago - Houston: Sun 8/02: £23
Go
5 days
£51
Tue 13 Jan - Sun 18 Jan
⌄
Houston - Chicago: Tue 13/01: £28
Go
Chicago - Houston: Sun 18/01: £23
Go
13 days
£51
Mon 12 Jan - Sun 25 Jan
⌄
Houston - Chicago: Mon 12/01: £28
Go
Chicago - Houston: Sun 25/01: £23
Go
11 days
£51
Mon 12 Jan - Fri 23 Jan
⌄
Houston - Chicago: Mon 12/01: £28
Go
Chicago - Houston: Fri 23/01: £23
Go
7 days
£51
Mon 12 Jan - Mon 19 Jan
⌄
Houston - Chicago: Mon 12/01: £28
Go
Chicago - Houston: Mon 19/01: £23
Go
6 days
£51
Mon 12 Jan - Sun 18 Jan
⌄
Houston - Chicago: Mon 12/01: £28
Go
Chicago - Houston: Sun 18/01: £23
Go
16 days
£51
Sun 11 Jan - Tue 27 Jan
⌄
Houston - Chicago: Sun 11/01: £23
Go
Chicago - Houston: Tue 27/01: £28
Go
15 days
£51
Sun 11 Jan - Mon 26 Jan
⌄
Houston - Chicago: Sun 11/01: £23
Go
Chicago - Houston: Mon 26/01: £28
Go
13 days
£51
Sun 11 Jan - Sat 24 Jan
⌄
Houston - Chicago: Sun 11/01: £23
Go
Chicago - Houston: Sat 24/01: £28
Go
11 days
£51
Sun 11 Jan - Thu 22 Jan
⌄
Houston - Chicago: Sun 11/01: £23
Go
Chicago - Houston: Thu 22/01: £28
Go
10 days
£51
Sun 11 Jan - Wed 21 Jan
⌄
Houston - Chicago: Sun 11/01: £23
Go
Chicago - Houston: Wed 21/01: £28
Go
15 days
£51
Sat 10 Jan - Sun 25 Jan
⌄
Houston - Chicago: Sat 10/01: £28
Go
Chicago - Houston: Sun 25/01: £23
Go
5 days
£51
Sun 25 Jan - Fri 30 Jan
⌄
Houston - Chicago: Sun 25/01: £23
Go
Chicago - Houston: Fri 30/01: £28
Go
13 days
£51
Sat 10 Jan - Fri 23 Jan
⌄
Houston - Chicago: Sat 10/01: £28
Go
Chicago - Houston: Fri 23/01: £23
Go
8 days
£51
Sat 10 Jan - Sun 18 Jan
⌄
Houston - Chicago: Sat 10/01: £28
Go
Chicago - Houston: Sun 18/01: £23
Go
16 days
£51
Fri 9 Jan - Sun 25 Jan
⌄
Houston - Chicago: Fri 9/01: £28
Go
Chicago - Houston: Sun 25/01: £23
Go
14 days
£51
Fri 9 Jan - Fri 23 Jan
⌄
Houston - Chicago: Fri 9/01: £28
Go
Chicago - Houston: Fri 23/01: £23
Go
10 days
£51
Fri 9 Jan - Mon 19 Jan
⌄
Houston - Chicago: Fri 9/01: £28
Go
Chicago - Houston: Mon 19/01: £23
Go
9 days
£51
Fri 9 Jan - Sun 18 Jan
⌄
Houston - Chicago: Fri 9/01: £28
Go
Chicago - Houston: Sun 18/01: £23
Go
15 days
£51
Thu 8 Jan - Fri 23 Jan
⌄
Houston - Chicago: Thu 8/01: £28
Go
Chicago - Houston: Fri 23/01: £23
Go
11 days
£51
Thu 8 Jan - Mon 19 Jan
⌄
Houston - Chicago: Thu 8/01: £28
Go
Chicago - Houston: Mon 19/01: £23
Go
10 days
£51
Thu 8 Jan - Sun 18 Jan
⌄
Houston - Chicago: Thu 8/01: £28
Go
Chicago - Houston: Sun 18/01: £23
Go
16 days
£51
Wed 7 Jan - Fri 23 Jan
⌄
Houston - Chicago: Wed 7/01: £28
Go
Chicago - Houston: Fri 23/01: £23
Go
12 days
£51
Wed 7 Jan - Mon 19 Jan
⌄
Houston - Chicago: Wed 7/01: £28
Go
Chicago - Houston: Mon 19/01: £23
Go
11 days
£51
Wed 7 Jan - Sun 18 Jan
⌄
Houston - Chicago: Wed 7/01: £28
Go
Chicago - Houston: Sun 18/01: £23
Go
9 days
£51
Sat 10 Jan - Mon 19 Jan
⌄
Houston - Chicago: Sat 10/01: £28
Go
Chicago - Houston: Mon 19/01: £23
Go
10 days
£51
Tue 13 Jan - Fri 23 Jan
⌄
Houston - Chicago: Tue 13/01: £28
Go
Chicago - Houston: Fri 23/01: £23
Go
6 days
£51
Tue 13 Jan - Mon 19 Jan
⌄
Houston - Chicago: Tue 13/01: £28
Go
Chicago - Houston: Mon 19/01: £23
Go
5 days
£51
Wed 14 Jan - Mon 19 Jan
⌄
Houston - Chicago: Wed 14/01: £28
Go
Chicago - Houston: Mon 19/01: £23
Go
13 days
£51
Sat 24 Jan - Fri 6 Feb
⌄
Houston - Chicago: Sat 24/01: £28
Go
Chicago - Houston: Fri 6/02: £23
Go
8 days
£51
Sat 24 Jan - Sun 1 Feb
⌄
Houston - Chicago: Sat 24/01: £28
Go
Chicago - Houston: Sun 1/02: £23
Go
13 days
£51
Fri 23 Jan - Thu 5 Feb
⌄
Houston - Chicago: Fri 23/01: £23
Go
Chicago - Houston: Thu 5/02: £28
Go
12 days
£51
Fri 23 Jan - Wed 4 Feb
⌄
Houston - Chicago: Fri 23/01: £23
Go
Chicago - Houston: Wed 4/02: £28
Go
11 days
£51
Fri 23 Jan - Tue 3 Feb
⌄
Houston - Chicago: Fri 23/01: £23
Go
Chicago - Houston: Tue 3/02: £28
Go
10 days
£51
Fri 23 Jan - Mon 2 Feb
⌄
Houston - Chicago: Fri 23/01: £23
Go
Chicago - Houston: Mon 2/02: £28
Go
8 days
£51
Fri 23 Jan - Sat 31 Jan
⌄
Houston - Chicago: Fri 23/01: £23
Go
Chicago - Houston: Sat 31/01: £28
Go
7 days
£51
Fri 23 Jan - Fri 30 Jan
⌄
Houston - Chicago: Fri 23/01: £23
Go
Chicago - Houston: Fri 30/01: £28
Go
6 days
£51
Fri 23 Jan - Thu 29 Jan
⌄
Houston - Chicago: Fri 23/01: £23
Go
Chicago - Houston: Thu 29/01: £28
Go
5 days
£51
Fri 23 Jan - Wed 28 Jan
⌄
Houston - Chicago: Fri 23/01: £23
Go
Chicago - Houston: Wed 28/01: £28
Go
12 days
£51
Tue 13 Jan - Sun 25 Jan
⌄
Houston - Chicago: Tue 13/01: £28
Go
Chicago - Houston: Sun 25/01: £23
Go
10 days
£51
Thu 22 Jan - Sun 1 Feb
⌄
Houston - Chicago: Thu 22/01: £28
Go
Chicago - Houston: Sun 1/02: £23
Go
15 days
£51
Thu 22 Jan - Fri 6 Feb
⌄
Houston - Chicago: Thu 22/01: £28
Go
Chicago - Houston: Fri 6/02: £23
Go
11 days
£51
Wed 21 Jan - Sun 1 Feb
⌄
Houston - Chicago: Wed 21/01: £28
Go
Chicago - Houston: Sun 1/02: £23
Go
9 days
£51
Wed 14 Jan - Fri 23 Jan
⌄
Houston - Chicago: Wed 14/01: £28
Go
Chicago - Houston: Fri 23/01: £23
Go
11 days
£51
Wed 14 Jan - Sun 25 Jan
⌄
Houston - Chicago: Wed 14/01: £28
Go
Chicago - Houston: Sun 25/01: £23
Go
6 days
£51
Sun 18 Jan - Sat 24 Jan
⌄
Houston - Chicago: Sun 18/01: £23
Go
Chicago - Houston: Sat 24/01: £28
Go
16 days
£51
Wed 21 Jan - Fri 6 Feb
⌄
Houston - Chicago: Wed 21/01: £28
Go
Chicago - Houston: Fri 6/02: £23
Go
9 days
£51
Sun 18 Jan - Tue 27 Jan
⌄
Houston - Chicago: Sun 18/01: £23
Go
Chicago - Houston: Tue 27/01: £28
Go
8 days
£51
Sun 18 Jan - Mon 26 Jan
⌄
Houston - Chicago: Sun 18/01: £23
Go
Chicago - Houston: Mon 26/01: £28
Go
11 days
£51
Sun 18 Jan - Thu 29 Jan
⌄
Houston - Chicago: Sun 18/01: £23
Go
Chicago - Houston: Thu 29/01: £28
Go
12 days
£51
Sun 18 Jan - Fri 30 Jan
⌄
Houston - Chicago: Sun 18/01: £23
Go
Chicago - Houston: Fri 30/01: £28
Go
13 days
£51
Sun 18 Jan - Sat 31 Jan
⌄
Houston - Chicago: Sun 18/01: £23
Go
Chicago - Houston: Sat 31/01: £28
Go
15 days
£51
Sun 18 Jan - Mon 2 Feb
⌄
Houston - Chicago: Sun 18/01: £23
Go
Chicago - Houston: Mon 2/02: £28
Go
16 days
£51
Sun 18 Jan - Tue 3 Feb
⌄
Houston - Chicago: Sun 18/01: £23
Go
Chicago - Houston: Tue 3/02: £28
Go
10 days
£51
Sun 18 Jan - Wed 28 Jan
⌄
Houston - Chicago: Sun 18/01: £23
Go
Chicago - Houston: Wed 28/01: £28
Go
14 days
£53
Thu 25 Dec - Thu 8 Jan
⌄
Houston - Chicago: Thu 25/12: £30
Go
Chicago - Houston: Thu 8/01: £23
Go
11 days
£54
Wed 31 Dec - Sun 11 Jan
⌄
Houston - Chicago: Wed 31/12: £31
Go
Chicago - Houston: Sun 11/01: £23
Go
8 days
£54
Wed 31 Dec - Thu 8 Jan
⌄
Houston - Chicago: Wed 31/12: £31
Go
Chicago - Houston: Thu 8/01: £23
Go
15 days
£54
Wed 24 Dec - Thu 8 Jan
⌄
Houston - Chicago: Wed 24/12: £31
Go
Chicago - Houston: Thu 8/01: £23
Go