Unlock hidden routes
Save on unique travels
Travel More, Pay Less! Unlock hidden routes and save on unique travels

Orlando & Chicago

from Houston

Best deal: £82

Orlando

Orlando, a city in central Florida, is known for its iconic theme parks, vibrant nightlife, and world-class dining. Visit the famous Walt Disney World, explore the magical Universal Orlando Resort, or enjoy the vibrant arts scene in Downtown Orlando. Orlando's lush golf courses, shopping outlets, and the annual Epcot International Flower & Garden Festival make it a city full of fun and excitement.

Chicago

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:

Orlando
&
Chicago
2 days
£82
11 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Fri 31/10: £26
Go
Chicago - Houston: Tue 11/11: £23
Go
⌄
Orlando
&
Chicago
2 days
£89
12 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Fri 31/10: £26
Go
Chicago - Houston: Wed 12/11: £30
Go
⌄
Orlando
&
Chicago
3 days
£89
11 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Fri 31/10: £26
Go
Chicago - Houston: Tue 11/11: £23
Go
⌄
Orlando
&
Chicago
2 days
£89
12 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Thu 30/10: £26
Go
Chicago - Houston: Tue 11/11: £23
Go
⌄
Orlando
&
Chicago
9 days
£89
4 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Fri 7/11: £33
Go
Chicago - Houston: Tue 11/11: £23
Go
⌄
Orlando
&
Chicago
8 days
£89
5 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Thu 6/11: £33
Go
Chicago - Houston: Tue 11/11: £23
Go
⌄
Orlando
&
Chicago
2 days
£92
6 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Fri 31/10: £26
Go
Chicago - Houston: Thu 6/11: £33
Go
⌄
Orlando
&
Chicago
10 days
£95
3 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Sat 8/11: £39
Go
Chicago - Houston: Tue 11/11: £23
Go
⌄
Orlando
&
Chicago
9 days
£96
5 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Thu 6/11: £33
Go
Chicago - Houston: Tue 11/11: £23
Go
⌄
Orlando
&
Chicago
10 days
£96
4 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Fri 7/11: £33
Go
Chicago - Houston: Tue 11/11: £23
Go
⌄
Orlando
&
Chicago
8 days
£96
6 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Thu 6/11: £33
Go
Chicago - Houston: Wed 12/11: £30
Go
⌄
Orlando
&
Chicago
9 days
£96
5 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Fri 7/11: £33
Go
Chicago - Houston: Wed 12/11: £30
Go
⌄
Orlando
&
Chicago
3 days
£96
12 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Fri 31/10: £26
Go
Chicago - Houston: Wed 12/11: £30
Go
⌄
Orlando
&
Chicago
2 days
£96
13 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Thu 30/10: £26
Go
Chicago - Houston: Wed 12/11: £30
Go
⌄
Orlando
&
Chicago
3 days
£99
6 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Fri 31/10: £26
Go
Chicago - Houston: Thu 6/11: £33
Go
⌄
Orlando
&
Chicago
2 days
£99
7 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Thu 30/10: £26
Go
Chicago - Houston: Thu 6/11: £33
Go
⌄
Orlando
&
Chicago
11 days
£102
3 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Sat 8/11: £39
Go
Chicago - Houston: Tue 11/11: £23
Go
⌄
Orlando
&
Chicago
10 days
£102
4 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Sat 8/11: £39
Go
Chicago - Houston: Wed 12/11: £30
Go
⌄
Orlando
&
Chicago
10 days
£103
5 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Fri 7/11: £33
Go
Chicago - Houston: Wed 12/11: £30
Go
⌄
Orlando
&
Chicago
9 days
£103
6 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Thu 6/11: £33
Go
Chicago - Houston: Wed 12/11: £30
Go
⌄
Orlando
&
Chicago
2 days
£104
8 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Fri 31/10: £26
Go
Chicago - Houston: Sat 8/11: £45
Go
⌄
Orlando
&
Chicago
2 days
£104
13 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Fri 31/10: £26
Go
Chicago - Houston: Thu 13/11: £45
Go
⌄
Orlando
&
Chicago
11 days
£109
4 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Sat 8/11: £39
Go
Chicago - Houston: Wed 12/11: £30
Go
⌄
Orlando
&
Chicago
8 days
£111
2 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Thu 6/11: £33
Go
Chicago - Houston: Sat 8/11: £45
Go
⌄
Orlando
&
Chicago
3 days
£111
8 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Fri 31/10: £26
Go
Chicago - Houston: Sat 8/11: £45
Go
⌄
Orlando
&
Chicago
2 days
£111
9 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Thu 30/10: £26
Go
Chicago - Houston: Sat 8/11: £45
Go
⌄
Orlando
&
Chicago
9 days
£111
6 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Fri 7/11: £33
Go
Chicago - Houston: Thu 13/11: £45
Go
⌄
Orlando
&
Chicago
8 days
£111
7 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Thu 6/11: £33
Go
Chicago - Houston: Thu 13/11: £45
Go
⌄
Orlando
&
Chicago
2 days
£115
10 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Fri 31/10: £26
Go
Chicago - Houston: Mon 10/11: £56
Go
⌄
Orlando
&
Chicago
2 days
£116
7 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Fri 31/10: £26
Go
Chicago - Houston: Fri 7/11: £57
Go
⌄
Orlando
&
Chicago
2 days
£116
9 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Fri 31/10: £26
Go
Chicago - Houston: Sun 9/11: £57
Go
⌄
Orlando
&
Chicago
10 days
£117
5 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Sat 8/11: £39
Go
Chicago - Houston: Thu 13/11: £45
Go
⌄
Orlando
&
Chicago
9 days
£118
2 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Thu 6/11: £33
Go
Chicago - Houston: Sat 8/11: £45
Go
⌄
Orlando
&
Chicago
2 days
£119
3 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Fri 31/10: £26
Go
Chicago - Houston: Mon 3/11: £60
Go
⌄
Orlando
&
Chicago
8 days
£122
4 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Thu 6/11: £33
Go
Chicago - Houston: Mon 10/11: £56
Go
⌄
Orlando
&
Chicago
9 days
£122
3 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Fri 7/11: £33
Go
Chicago - Houston: Mon 10/11: £56
Go
⌄
Orlando
&
Chicago
2 days
£122
2 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Thu 30/10: £26
Go
Chicago - Houston: Sat 1/11: £56
Go
⌄
Orlando
&
Chicago
2 days
£122
11 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Thu 30/10: £26
Go
Chicago - Houston: Mon 10/11: £56
Go
⌄
Orlando
&
Chicago
3 days
£122
10 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Fri 31/10: £26
Go
Chicago - Houston: Mon 10/11: £56
Go
⌄
Orlando
&
Chicago
3 days
£123
9 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Fri 31/10: £26
Go
Chicago - Houston: Sun 9/11: £57
Go
⌄
Orlando
&
Chicago
2 days
£123
10 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Thu 30/10: £26
Go
Chicago - Houston: Sun 9/11: £57
Go
⌄
Orlando
&
Chicago
9 days
£123
2 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Fri 7/11: £33
Go
Chicago - Houston: Sun 9/11: £57
Go
⌄
Orlando
&
Chicago
2 days
£123
8 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Thu 30/10: £26
Go
Chicago - Houston: Fri 7/11: £57
Go
⌄
Orlando
&
Chicago
8 days
£123
3 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Thu 6/11: £33
Go
Chicago - Houston: Sun 9/11: £57
Go
⌄
Orlando
&
Chicago
3 days
£123
7 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Fri 31/10: £26
Go
Chicago - Houston: Fri 7/11: £57
Go
⌄
Orlando
&
Chicago
3 days
£126
3 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Fri 31/10: £26
Go
Chicago - Houston: Mon 3/11: £60
Go
⌄
Orlando
&
Chicago
2 days
£126
4 days
Houston - Orlando: Tue 28/10: £40
Go
Orlando - Chicago: Thu 30/10: £26
Go
Chicago - Houston: Mon 3/11: £60
Go
⌄
Orlando
&
Chicago
2 days
£127
5 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Fri 31/10: £26
Go
Chicago - Houston: Wed 5/11: £68
Go
⌄
Orlando
&
Chicago
2 days
£127
4 days
Houston - Orlando: Wed 29/10: £33
Go
Orlando - Chicago: Fri 31/10: £26
Go
Chicago - Houston: Tue 4/11: £68
Go
⌄