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Chicago

from Orlando

Save up to: £123

Average cost: £167

Best deal: £44

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
£44
Thu 15 Jan - Sun 18 Jan
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Orlando - Chicago: Thu 15/01: £22
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Chicago - Orlando: Sun 18/01: £22
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4 days
£44
Sat 21 Feb - Wed 25 Feb
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Orlando - Chicago: Sat 21/02: £22
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Chicago - Orlando: Wed 25/02: £22
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3 days
£44
Sat 21 Feb - Tue 24 Feb
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Orlando - Chicago: Sat 21/02: £22
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Chicago - Orlando: Tue 24/02: £22
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4 days
£47
Thu 15 Jan - Mon 19 Jan
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Orlando - Chicago: Thu 15/01: £22
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Chicago - Orlando: Mon 19/01: £25
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2 days
£47
Sat 17 Jan - Mon 19 Jan
⌄
Orlando - Chicago: Sat 17/01: £22
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Chicago - Orlando: Mon 19/01: £25
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3 days
£48
Tue 10 Feb - Fri 13 Feb
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Orlando - Chicago: Tue 10/02: £22
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Chicago - Orlando: Fri 13/02: £26
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5 days
£48
Tue 10 Feb - Sun 15 Feb
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Orlando - Chicago: Tue 10/02: £22
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Chicago - Orlando: Sun 15/02: £26
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2 days
£48
Wed 11 Feb - Fri 13 Feb
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Orlando - Chicago: Wed 11/02: £22
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Chicago - Orlando: Fri 13/02: £26
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4 days
£48
Wed 11 Feb - Sun 15 Feb
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Orlando - Chicago: Wed 11/02: £22
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Chicago - Orlando: Sun 15/02: £26
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5 days
£48
Wed 11 Feb - Mon 16 Feb
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Orlando - Chicago: Wed 11/02: £22
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Chicago - Orlando: Mon 16/02: £26
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2 days
£48
Thu 19 Feb - Sat 21 Feb
⌄
Orlando - Chicago: Thu 19/02: £26
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Chicago - Orlando: Sat 21/02: £22
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5 days
£48
Thu 19 Feb - Tue 24 Feb
⌄
Orlando - Chicago: Thu 19/02: £26
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Chicago - Orlando: Tue 24/02: £22
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2 days
£48
Sat 21 Feb - Mon 23 Feb
⌄
Orlando - Chicago: Sat 21/02: £22
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Chicago - Orlando: Mon 23/02: £26
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2 days
£48
Thu 26 Feb - Sat 28 Feb
⌄
Orlando - Chicago: Thu 26/02: £26
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Chicago - Orlando: Sat 28/02: £22
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3 days
£50
Thu 5 Feb - Sun 8 Feb
⌄
Orlando - Chicago: Thu 5/02: £25
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Chicago - Orlando: Sun 8/02: £25
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3 days
£50
Fri 30 Jan - Mon 2 Feb
⌄
Orlando - Chicago: Fri 30/01: £25
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Chicago - Orlando: Mon 2/02: £25
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2 days
£50
Fri 30 Jan - Sun 1 Feb
⌄
Orlando - Chicago: Fri 30/01: £25
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Chicago - Orlando: Sun 1/02: £25
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4 days
£50
Thu 29 Jan - Mon 2 Feb
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Orlando - Chicago: Thu 29/01: £25
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Chicago - Orlando: Mon 2/02: £25
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3 days
£50
Thu 29 Jan - Sun 1 Feb
⌄
Orlando - Chicago: Thu 29/01: £25
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Chicago - Orlando: Sun 1/02: £25
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2 days
£50
Fri 6 Feb - Sun 8 Feb
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Orlando - Chicago: Fri 6/02: £25
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Chicago - Orlando: Sun 8/02: £25
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4 days
£50
Thu 22 Jan - Mon 26 Jan
⌄
Orlando - Chicago: Thu 22/01: £25
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Chicago - Orlando: Mon 26/01: £25
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3 days
£50
Fri 23 Jan - Mon 26 Jan
⌄
Orlando - Chicago: Fri 23/01: £25
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Chicago - Orlando: Mon 26/01: £25
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4 days
£51
Thu 12 Feb - Mon 16 Feb
⌄
Orlando - Chicago: Thu 12/02: £25
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Chicago - Orlando: Mon 16/02: £26
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5 days
£51
Thu 15 Jan - Tue 20 Jan
⌄
Orlando - Chicago: Thu 15/01: £22
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Chicago - Orlando: Tue 20/01: £29
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3 days
£51
Wed 25 Feb - Sat 28 Feb
⌄
Orlando - Chicago: Wed 25/02: £29
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Chicago - Orlando: Sat 28/02: £22
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4 days
£51
Tue 24 Feb - Sat 28 Feb
⌄
Orlando - Chicago: Tue 24/02: £29
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Chicago - Orlando: Sat 28/02: £22
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3 days
£51
Sat 17 Jan - Tue 20 Jan
⌄
Orlando - Chicago: Sat 17/01: £22
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Chicago - Orlando: Tue 20/01: £29
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4 days
£51
Sat 17 Jan - Wed 21 Jan
⌄
Orlando - Chicago: Sat 17/01: £22
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Chicago - Orlando: Wed 21/01: £29
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3 days
£51
Thu 12 Feb - Sun 15 Feb
⌄
Orlando - Chicago: Thu 12/02: £25
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Chicago - Orlando: Sun 15/02: £26
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4 days
£51
Thu 5 Feb - Mon 9 Feb
⌄
Orlando - Chicago: Thu 5/02: £25
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Chicago - Orlando: Mon 9/02: £26
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3 days
£51
Fri 6 Feb - Mon 9 Feb
⌄
Orlando - Chicago: Fri 6/02: £25
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Chicago - Orlando: Mon 9/02: £26
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4 days
£52
Thu 19 Feb - Mon 23 Feb
⌄
Orlando - Chicago: Thu 19/02: £26
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Chicago - Orlando: Mon 23/02: £26
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3 days
£52
Thu 19 Feb - Sun 22 Feb
⌄
Orlando - Chicago: Thu 19/02: £26
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Chicago - Orlando: Sun 22/02: £26
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3 days
£52
Fri 13 Feb - Mon 16 Feb
⌄
Orlando - Chicago: Fri 13/02: £26
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Chicago - Orlando: Mon 16/02: £26
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2 days
£52
Fri 13 Feb - Sun 15 Feb
⌄
Orlando - Chicago: Fri 13/02: £26
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Chicago - Orlando: Sun 15/02: £26
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2 days
£52
Fri 27 Feb - Sun 1 Mar
⌄
Orlando - Chicago: Fri 27/02: £26
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Chicago - Orlando: Sun 1/03: £26
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3 days
£52
Thu 26 Feb - Sun 1 Mar
⌄
Orlando - Chicago: Thu 26/02: £26
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Chicago - Orlando: Sun 1/03: £26
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4 days
£54
Fri 6 Feb - Tue 10 Feb
⌄
Orlando - Chicago: Fri 6/02: £25
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Chicago - Orlando: Tue 10/02: £29
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5 days
£54
Thu 29 Jan - Tue 3 Feb
⌄
Orlando - Chicago: Thu 29/01: £25
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Chicago - Orlando: Tue 3/02: £29
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4 days
£54
Wed 28 Jan - Sun 1 Feb
⌄
Orlando - Chicago: Wed 28/01: £29
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Chicago - Orlando: Sun 1/02: £25
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5 days
£54
Tue 27 Jan - Sun 1 Feb
⌄
Orlando - Chicago: Tue 27/01: £29
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Chicago - Orlando: Sun 1/02: £25
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4 days
£54
Fri 30 Jan - Tue 3 Feb
⌄
Orlando - Chicago: Fri 30/01: £25
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Chicago - Orlando: Tue 3/02: £29
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5 days
£54
Fri 30 Jan - Wed 4 Feb
⌄
Orlando - Chicago: Fri 30/01: £25
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Chicago - Orlando: Wed 4/02: £29
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5 days
£54
Wed 21 Jan - Mon 26 Jan
⌄
Orlando - Chicago: Wed 21/01: £29
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Chicago - Orlando: Mon 26/01: £25
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2 days
£54
Sat 31 Jan - Mon 2 Feb
⌄
Orlando - Chicago: Sat 31/01: £29
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Chicago - Orlando: Mon 2/02: £25
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2 days
£54
Thu 22 Jan - Sat 24 Jan
⌄
Orlando - Chicago: Thu 22/01: £25
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Chicago - Orlando: Sat 24/01: £29
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4 days
£54
Wed 4 Feb - Sun 8 Feb
⌄
Orlando - Chicago: Wed 4/02: £29
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Chicago - Orlando: Sun 8/02: £25
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5 days
£54
Tue 3 Feb - Sun 8 Feb
⌄
Orlando - Chicago: Tue 3/02: £29
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Chicago - Orlando: Sun 8/02: £25
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5 days
£54
Thu 5 Feb - Tue 10 Feb
⌄
Orlando - Chicago: Thu 5/02: £25
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Chicago - Orlando: Tue 10/02: £29
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5 days
£54
Fri 23 Jan - Wed 28 Jan
⌄
Orlando - Chicago: Fri 23/01: £25
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Chicago - Orlando: Wed 28/01: £29
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4 days
£54
Fri 23 Jan - Tue 27 Jan
⌄
Orlando - Chicago: Fri 23/01: £25
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Chicago - Orlando: Tue 27/01: £29
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5 days
£54
Thu 22 Jan - Tue 27 Jan
⌄
Orlando - Chicago: Thu 22/01: £25
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Chicago - Orlando: Tue 27/01: £29
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2 days
£54
Sat 24 Jan - Mon 26 Jan
⌄
Orlando - Chicago: Sat 24/01: £29
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Chicago - Orlando: Mon 26/01: £25
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5 days
£54
Wed 28 Jan - Mon 2 Feb
⌄
Orlando - Chicago: Wed 28/01: £29
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Chicago - Orlando: Mon 2/02: £25
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2 days
£54
Thu 29 Jan - Sat 31 Jan
⌄
Orlando - Chicago: Thu 29/01: £25
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Chicago - Orlando: Sat 31/01: £29
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5 days
£54
Thu 12 Feb - Tue 17 Feb
⌄
Orlando - Chicago: Thu 12/02: £25
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Chicago - Orlando: Tue 17/02: £29
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2 days
£54
Thu 5 Feb - Sat 7 Feb
⌄
Orlando - Chicago: Thu 5/02: £25
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Chicago - Orlando: Sat 7/02: £29
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4 days
£55
Fri 20 Feb - Tue 24 Feb
⌄
Orlando - Chicago: Fri 20/02: £33
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Chicago - Orlando: Tue 24/02: £22
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5 days
£55
Fri 20 Feb - Wed 25 Feb
⌄
Orlando - Chicago: Fri 20/02: £33
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Chicago - Orlando: Wed 25/02: £22
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5 days
£55
Wed 4 Feb - Mon 9 Feb
⌄
Orlando - Chicago: Wed 4/02: £29
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Chicago - Orlando: Mon 9/02: £26
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2 days
£55
Fri 16 Jan - Sun 18 Jan
⌄
Orlando - Chicago: Fri 16/01: £33
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Chicago - Orlando: Sun 18/01: £22
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2 days
£55
Mon 23 Feb - Wed 25 Feb
⌄
Orlando - Chicago: Mon 23/02: £33
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Chicago - Orlando: Wed 25/02: £22
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5 days
£55
Mon 23 Feb - Sat 28 Feb
⌄
Orlando - Chicago: Mon 23/02: £33
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Chicago - Orlando: Sat 28/02: £22
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3 days
£55
Wed 18 Feb - Sat 21 Feb
⌄
Orlando - Chicago: Wed 18/02: £33
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Chicago - Orlando: Sat 21/02: £22
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5 days
£55
Tue 24 Feb - Sun 1 Mar
⌄
Orlando - Chicago: Tue 24/02: £29
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Chicago - Orlando: Sun 1/03: £26
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5 days
£55
Fri 13 Feb - Wed 18 Feb
⌄
Orlando - Chicago: Fri 13/02: £26
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Chicago - Orlando: Wed 18/02: £29
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4 days
£55
Wed 25 Feb - Sun 1 Mar
⌄
Orlando - Chicago: Wed 25/02: £29
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Chicago - Orlando: Sun 1/03: £26
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2 days
£55
Sat 7 Feb - Mon 9 Feb
⌄
Orlando - Chicago: Sat 7/02: £29
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Chicago - Orlando: Mon 9/02: £26
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4 days
£55
Fri 13 Feb - Tue 17 Feb
⌄
Orlando - Chicago: Fri 13/02: £26
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Chicago - Orlando: Tue 17/02: £29
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