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Chicago

from Washington D.C.

Save up to: £143

Average cost: £175

Best deal: £32

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:

14 days
£32
Wed 19 Mar - Wed 2 Apr
⌄
Washington D.C. - Chicago: Wed 19/03: £16
Chicago - Washington D.C.: Wed 2/04: £16
Go
7 days
£32
Wed 5 Mar - Wed 12 Mar
⌄
Washington D.C. - Chicago: Wed 5/03: £16
Chicago - Washington D.C.: Wed 12/03: £16
Go
5 days
£32
Wed 5 Mar - Mon 10 Mar
⌄
Washington D.C. - Chicago: Wed 5/03: £16
Chicago - Washington D.C.: Mon 10/03: £16
Go
9 days
£32
Mon 3 Mar - Wed 12 Mar
⌄
Washington D.C. - Chicago: Mon 3/03: £16
Chicago - Washington D.C.: Wed 12/03: £16
Go
7 days
£32
Mon 3 Mar - Mon 10 Mar
⌄
Washington D.C. - Chicago: Mon 3/03: £16
Chicago - Washington D.C.: Mon 10/03: £16
Go
14 days
£32
Wed 26 Feb - Wed 12 Mar
⌄
Washington D.C. - Chicago: Wed 26/02: £16
Chicago - Washington D.C.: Wed 12/03: £16
Go
12 days
£32
Wed 26 Feb - Mon 10 Mar
⌄
Washington D.C. - Chicago: Wed 26/02: £16
Chicago - Washington D.C.: Mon 10/03: £16
Go
7 days
£32
Wed 26 Feb - Wed 5 Mar
⌄
Washington D.C. - Chicago: Wed 26/02: £16
Chicago - Washington D.C.: Wed 5/03: £16
Go
7 days
£33
Sat 22 Feb - Sat 1 Mar
⌄
Washington D.C. - Chicago: Sat 22/02: £17
Chicago - Washington D.C.: Sat 1/03: £16
Go
11 days
£33
Sat 22 Feb - Wed 5 Mar
⌄
Washington D.C. - Chicago: Sat 22/02: £17
Chicago - Washington D.C.: Wed 5/03: £16
Go
16 days
£33
Sat 22 Feb - Mon 10 Mar
⌄
Washington D.C. - Chicago: Sat 22/02: £17
Chicago - Washington D.C.: Mon 10/03: £16
Go
14 days
£36
Wed 12 Feb - Wed 26 Feb
⌄
Washington D.C. - Chicago: Wed 12/02: £20
Chicago - Washington D.C.: Wed 26/02: £16
Go
10 days
£37
Wed 12 Feb - Sat 22 Feb
⌄
Washington D.C. - Chicago: Wed 12/02: £20
Chicago - Washington D.C.: Sat 22/02: £17
Go
16 days
£40
Mon 24 Mar - Wed 9 Apr
⌄
Washington D.C. - Chicago: Mon 24/03: £24
Chicago - Washington D.C.: Wed 9/04: £16
Go
9 days
£40
Mon 24 Mar - Wed 2 Apr
⌄
Washington D.C. - Chicago: Mon 24/03: £24
Chicago - Washington D.C.: Wed 2/04: £16
Go
16 days
£40
Mon 17 Mar - Wed 2 Apr
⌄
Washington D.C. - Chicago: Mon 17/03: £24
Chicago - Washington D.C.: Wed 2/04: £16
Go
12 days
£40
Wed 19 Mar - Mon 31 Mar
⌄
Washington D.C. - Chicago: Wed 19/03: £16
Chicago - Washington D.C.: Mon 31/03: £24
Go
14 days
£40
Mon 24 Feb - Mon 10 Mar
⌄
Washington D.C. - Chicago: Mon 24/02: £24
Chicago - Washington D.C.: Mon 10/03: £16
Go
9 days
£40
Mon 24 Feb - Wed 5 Mar
⌄
Washington D.C. - Chicago: Mon 24/02: £24
Chicago - Washington D.C.: Wed 5/03: £16
Go
5 days
£40
Mon 24 Feb - Sat 1 Mar
⌄
Washington D.C. - Chicago: Mon 24/02: £24
Chicago - Washington D.C.: Sat 1/03: £16
Go
16 days
£40
Mon 24 Feb - Wed 12 Mar
⌄
Washington D.C. - Chicago: Mon 24/02: £24
Chicago - Washington D.C.: Wed 12/03: £16
Go
12 days
£44
Wed 12 Feb - Mon 24 Feb
⌄
Washington D.C. - Chicago: Wed 12/02: £20
Chicago - Washington D.C.: Mon 24/02: £24
Go
7 days
£45
Wed 19 Feb - Wed 26 Feb
⌄
Washington D.C. - Chicago: Wed 19/02: £29
Chicago - Washington D.C.: Wed 26/02: £16
Go
10 days
£45
Wed 19 Feb - Sat 1 Mar
⌄
Washington D.C. - Chicago: Wed 19/02: £29
Chicago - Washington D.C.: Sat 1/03: £16
Go
14 days
£45
Wed 19 Feb - Wed 5 Mar
⌄
Washington D.C. - Chicago: Wed 19/02: £29
Chicago - Washington D.C.: Wed 5/03: £16
Go
14 days
£48
Mon 17 Mar - Mon 31 Mar
⌄
Washington D.C. - Chicago: Mon 17/03: £24
Chicago - Washington D.C.: Mon 31/03: £24
Go
14 days
£48
Thu 1 May - Thu 15 May
⌄
Washington D.C. - Chicago: Thu 1/05: £24
Chicago - Washington D.C.: Thu 15/05: £24
Go
9 days
£48
Sat 1 Mar - Mon 10 Mar
⌄
Washington D.C. - Chicago: Sat 1/03: £32
Chicago - Washington D.C.: Mon 10/03: £16
Go
7 days
£48
Mon 24 Mar - Mon 31 Mar
⌄
Washington D.C. - Chicago: Mon 24/03: £24
Chicago - Washington D.C.: Mon 31/03: £24
Go
10 days
£48
Mon 5 May - Thu 15 May
⌄
Washington D.C. - Chicago: Mon 5/05: £24
Chicago - Washington D.C.: Thu 15/05: £24
Go
7 days
£48
Thu 1 May - Thu 8 May
⌄
Washington D.C. - Chicago: Thu 1/05: £24
Chicago - Washington D.C.: Thu 8/05: £24
Go
14 days
£48
Mon 24 Mar - Mon 7 Apr
⌄
Washington D.C. - Chicago: Mon 24/03: £24
Chicago - Washington D.C.: Mon 7/04: £24
Go
11 days
£48
Sat 1 Mar - Wed 12 Mar
⌄
Washington D.C. - Chicago: Sat 1/03: £32
Chicago - Washington D.C.: Wed 12/03: £16
Go
7 days
£48
Thu 8 May - Thu 15 May
⌄
Washington D.C. - Chicago: Thu 8/05: £24
Chicago - Washington D.C.: Thu 15/05: £24
Go
9 days
£49
Mon 7 Apr - Wed 16 Apr
⌄
Washington D.C. - Chicago: Mon 7/04: £24
Chicago - Washington D.C.: Wed 16/04: £25
Go
7 days
£49
Wed 12 Feb - Wed 19 Feb
⌄
Washington D.C. - Chicago: Wed 12/02: £20
Chicago - Washington D.C.: Wed 19/02: £29
Go
9 days
£52
Wed 26 Feb - Fri 7 Mar
⌄
Washington D.C. - Chicago: Wed 26/02: £16
Chicago - Washington D.C.: Fri 7/03: £36
Go
5 days
£52
Wed 26 Feb - Mon 3 Mar
⌄
Washington D.C. - Chicago: Wed 26/02: £16
Chicago - Washington D.C.: Mon 3/03: £36
Go
5 days
£52
Fri 7 Mar - Wed 12 Mar
⌄
Washington D.C. - Chicago: Fri 7/03: £36
Chicago - Washington D.C.: Wed 12/03: £16
Go
13 days
£53
Sat 22 Feb - Fri 7 Mar
⌄
Washington D.C. - Chicago: Sat 22/02: £17
Chicago - Washington D.C.: Fri 7/03: £36
Go
9 days
£53
Sat 22 Feb - Mon 3 Mar
⌄
Washington D.C. - Chicago: Sat 22/02: £17
Chicago - Washington D.C.: Mon 3/03: £36
Go
5 days
£53
Wed 19 Feb - Mon 24 Feb
⌄
Washington D.C. - Chicago: Wed 19/02: £29
Chicago - Washington D.C.: Mon 24/02: £24
Go
12 days
£56
Fri 28 Feb - Wed 12 Mar
⌄
Washington D.C. - Chicago: Fri 28/02: £40
Chicago - Washington D.C.: Wed 12/03: £16
Go
5 days
£56
Fri 28 Feb - Wed 5 Mar
⌄
Washington D.C. - Chicago: Fri 28/02: £40
Chicago - Washington D.C.: Wed 5/03: £16
Go
7 days
£56
Mon 28 Apr - Mon 5 May
⌄
Washington D.C. - Chicago: Mon 28/04: £32
Chicago - Washington D.C.: Mon 5/05: £24
Go
10 days
£56
Mon 28 Apr - Thu 8 May
⌄
Washington D.C. - Chicago: Mon 28/04: £32
Chicago - Washington D.C.: Thu 8/05: £24
Go
10 days
£56
Fri 28 Feb - Mon 10 Mar
⌄
Washington D.C. - Chicago: Fri 28/02: £40
Chicago - Washington D.C.: Mon 10/03: £16
Go