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

Chicago & Boston

from Orlando

Best deal: £112

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.

Boston

Boston, one of the oldest cities in the U.S., is known for its rich history, prestigious universities, and diverse neighborhoods. Visit the historic Freedom Trail, explore the bustling Faneuil Hall Marketplace, or catch a game at Fenway Park. Boston's clam chowder, vibrant arts scene, and the annual Boston Marathon make it a city of tradition and innovation.

Latest deals:

Chicago
&
Boston
10 days
£112
2 days
Orlando - Chicago: Sat 25/04: £33
Go
Chicago - Boston: Tue 5/05: £42
Go
Boston - Orlando: Thu 7/05: £37
Go
⌄
Chicago
&
Boston
4 days
£112
7 days
Orlando - Chicago: Sat 25/04: £33
Go
Chicago - Boston: Wed 29/04: £42
Go
Boston - Orlando: Wed 6/05: £37
Go
⌄
Chicago
&
Boston
4 days
£112
6 days
Orlando - Chicago: Sat 25/04: £33
Go
Chicago - Boston: Wed 29/04: £42
Go
Boston - Orlando: Tue 5/05: £37
Go
⌄
Chicago
&
Boston
4 days
£112
5 days
Orlando - Chicago: Sat 25/04: £33
Go
Chicago - Boston: Wed 29/04: £42
Go
Boston - Orlando: Mon 4/05: £37
Go
⌄
Chicago
&
Boston
4 days
£112
3 days
Orlando - Chicago: Sat 25/04: £33
Go
Chicago - Boston: Wed 29/04: £42
Go
Boston - Orlando: Sat 2/05: £37
Go
⌄
Chicago
&
Boston
4 days
£112
8 days
Orlando - Chicago: Sat 25/04: £33
Go
Chicago - Boston: Wed 29/04: £42
Go
Boston - Orlando: Thu 7/05: £37
Go
⌄
Chicago
&
Boston
5 days
£163
6 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Tue 3/03: £54
Go
Boston - Orlando: Mon 9/03: £41
Go
⌄
Chicago
&
Boston
6 days
£163
5 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Wed 4/03: £54
Go
Boston - Orlando: Mon 9/03: £41
Go
⌄
Chicago
&
Boston
7 days
£163
4 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Thu 5/03: £54
Go
Boston - Orlando: Mon 9/03: £41
Go
⌄
Chicago
&
Boston
3 days
£163
9 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Sun 1/03: £54
Go
Boston - Orlando: Tue 10/03: £41
Go
⌄
Chicago
&
Boston
4 days
£163
8 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Mon 2/03: £54
Go
Boston - Orlando: Tue 10/03: £41
Go
⌄
Chicago
&
Boston
5 days
£163
7 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Tue 3/03: £54
Go
Boston - Orlando: Tue 10/03: £41
Go
⌄
Chicago
&
Boston
3 days
£163
10 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Sun 1/03: £54
Go
Boston - Orlando: Wed 11/03: £41
Go
⌄
Chicago
&
Boston
4 days
£163
7 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Mon 2/03: £54
Go
Boston - Orlando: Mon 9/03: £41
Go
⌄
Chicago
&
Boston
4 days
£163
9 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Mon 2/03: £54
Go
Boston - Orlando: Wed 11/03: £41
Go
⌄
Chicago
&
Boston
5 days
£163
8 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Tue 3/03: £54
Go
Boston - Orlando: Wed 11/03: £41
Go
⌄
Chicago
&
Boston
6 days
£163
7 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Wed 4/03: £54
Go
Boston - Orlando: Wed 11/03: £41
Go
⌄
Chicago
&
Boston
7 days
£163
6 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Thu 5/03: £54
Go
Boston - Orlando: Wed 11/03: £41
Go
⌄
Chicago
&
Boston
11 days
£163
2 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Mon 9/03: £54
Go
Boston - Orlando: Wed 11/03: £41
Go
⌄
Chicago
&
Boston
6 days
£163
6 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Wed 4/03: £54
Go
Boston - Orlando: Tue 10/03: £41
Go
⌄
Chicago
&
Boston
3 days
£163
8 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Sun 1/03: £54
Go
Boston - Orlando: Mon 9/03: £41
Go
⌄
Chicago
&
Boston
7 days
£163
5 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Thu 5/03: £54
Go
Boston - Orlando: Tue 10/03: £41
Go
⌄
Chicago
&
Boston
8 days
£169
5 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Fri 6/03: £60
Go
Boston - Orlando: Wed 11/03: £41
Go
⌄
Chicago
&
Boston
8 days
£169
3 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Fri 6/03: £60
Go
Boston - Orlando: Mon 9/03: £41
Go
⌄
Chicago
&
Boston
8 days
£169
4 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Fri 6/03: £60
Go
Boston - Orlando: Tue 10/03: £41
Go
⌄
Chicago
&
Boston
3 days
£189
2 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Sun 1/03: £54
Go
Boston - Orlando: Tue 3/03: £67
Go
⌄
Chicago
&
Boston
2 days
£190
10 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Sat 28/02: £81
Go
Boston - Orlando: Tue 10/03: £41
Go
⌄
Chicago
&
Boston
2 days
£190
9 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Sat 28/02: £81
Go
Boston - Orlando: Mon 9/03: £41
Go
⌄
Chicago
&
Boston
2 days
£190
11 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Sat 28/02: £81
Go
Boston - Orlando: Wed 11/03: £41
Go
⌄
Chicago
&
Boston
9 days
£193
4 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Sat 7/03: £84
Go
Boston - Orlando: Wed 11/03: £41
Go
⌄
Chicago
&
Boston
9 days
£193
2 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Sat 7/03: £84
Go
Boston - Orlando: Mon 9/03: £41
Go
⌄
Chicago
&
Boston
9 days
£193
3 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Sat 7/03: £84
Go
Boston - Orlando: Tue 10/03: £41
Go
⌄
Chicago
&
Boston
7 days
£207
7 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Thu 5/03: £54
Go
Boston - Orlando: Thu 12/03: £85
Go
⌄
Chicago
&
Boston
6 days
£207
8 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Wed 4/03: £54
Go
Boston - Orlando: Thu 12/03: £85
Go
⌄
Chicago
&
Boston
5 days
£207
9 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Tue 3/03: £54
Go
Boston - Orlando: Thu 12/03: £85
Go
⌄
Chicago
&
Boston
4 days
£207
10 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Mon 2/03: £54
Go
Boston - Orlando: Thu 12/03: £85
Go
⌄
Chicago
&
Boston
3 days
£207
11 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Sun 1/03: £54
Go
Boston - Orlando: Thu 12/03: £85
Go
⌄
Chicago
&
Boston
11 days
£207
3 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Mon 9/03: £54
Go
Boston - Orlando: Thu 12/03: £85
Go
⌄
Chicago
&
Boston
12 days
£207
2 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Tue 10/03: £54
Go
Boston - Orlando: Thu 12/03: £85
Go
⌄
Chicago
&
Boston
4 days
£207
11 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Mon 2/03: £54
Go
Boston - Orlando: Fri 13/03: £85
Go
⌄
Chicago
&
Boston
4 days
£207
2 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Mon 2/03: £54
Go
Boston - Orlando: Wed 4/03: £85
Go
⌄
Chicago
&
Boston
5 days
£207
10 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Tue 3/03: £54
Go
Boston - Orlando: Fri 13/03: £85
Go
⌄
Chicago
&
Boston
6 days
£207
9 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Wed 4/03: £54
Go
Boston - Orlando: Fri 13/03: £85
Go
⌄
Chicago
&
Boston
7 days
£207
8 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Thu 5/03: £54
Go
Boston - Orlando: Fri 13/03: £85
Go
⌄
Chicago
&
Boston
11 days
£207
4 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Mon 9/03: £54
Go
Boston - Orlando: Fri 13/03: £85
Go
⌄
Chicago
&
Boston
12 days
£207
3 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Tue 10/03: £54
Go
Boston - Orlando: Fri 13/03: £85
Go
⌄
Chicago
&
Boston
13 days
£207
2 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Wed 11/03: £54
Go
Boston - Orlando: Fri 13/03: £85
Go
⌄
Chicago
&
Boston
3 days
£207
3 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Sun 1/03: £54
Go
Boston - Orlando: Wed 4/03: £85
Go
⌄
Chicago
&
Boston
3 days
£207
12 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Sun 1/03: £54
Go
Boston - Orlando: Fri 13/03: £85
Go
⌄
Chicago
&
Boston
8 days
£213
6 days
Orlando - Chicago: Thu 26/02: £68
Go
Chicago - Boston: Fri 6/03: £60
Go
Boston - Orlando: Thu 12/03: £85
Go
⌄

... 34 more possible dates exist ...