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Chicago

from Orlando

Save up to: £169

Average cost: £252

Best deal: £83

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:

6 days
£83
Wed 19 Aug - Tue 25 Aug
⌄
Orlando - Chicago: Wed 19/08: £38
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Chicago - Orlando: Tue 25/08: £45
Go
7 days
£83
Wed 19 Aug - Wed 26 Aug
⌄
Orlando - Chicago: Wed 19/08: £38
Go
Chicago - Orlando: Wed 26/08: £45
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13 days
£83
Wed 19 Aug - Tue 1 Sep
⌄
Orlando - Chicago: Wed 19/08: £38
Go
Chicago - Orlando: Tue 1/09: £45
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7 days
£83
Tue 25 Aug - Tue 1 Sep
⌄
Orlando - Chicago: Tue 25/08: £38
Go
Chicago - Orlando: Tue 1/09: £45
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14 days
£83
Tue 25 Aug - Tue 8 Sep
⌄
Orlando - Chicago: Tue 25/08: £38
Go
Chicago - Orlando: Tue 8/09: £45
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15 days
£83
Tue 25 Aug - Wed 9 Sep
⌄
Orlando - Chicago: Tue 25/08: £38
Go
Chicago - Orlando: Wed 9/09: £45
Go
6 days
£83
Wed 26 Aug - Tue 1 Sep
⌄
Orlando - Chicago: Wed 26/08: £38
Go
Chicago - Orlando: Tue 1/09: £45
Go
13 days
£83
Wed 26 Aug - Tue 8 Sep
⌄
Orlando - Chicago: Wed 26/08: £38
Go
Chicago - Orlando: Tue 8/09: £45
Go
14 days
£83
Wed 26 Aug - Wed 9 Sep
⌄
Orlando - Chicago: Wed 26/08: £38
Go
Chicago - Orlando: Wed 9/09: £45
Go
6 days
£83
Wed 9 Sep - Tue 15 Sep
⌄
Orlando - Chicago: Wed 9/09: £38
Go
Chicago - Orlando: Tue 15/09: £45
Go
13 days
£83
Wed 9 Sep - Tue 22 Sep
⌄
Orlando - Chicago: Wed 9/09: £38
Go
Chicago - Orlando: Tue 22/09: £45
Go