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Chicago & Orlando

from Portland

Best deal: £217

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.

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.

Latest deals:

Chicago
&
Orlando
11 days
£217
4 days
Portland - Chicago: Tue 24/03: £43
Go
Chicago - Orlando: Sat 4/04: £35
Go
Orlando - Portland: Wed 8/04: £139
Go
⌄
Chicago
&
Orlando
11 days
£217
3 days
Portland - Chicago: Tue 24/03: £43
Go
Chicago - Orlando: Sat 4/04: £35
Go
Orlando - Portland: Tue 7/04: £139
Go
⌄
Chicago
&
Orlando
11 days
£217
2 days
Portland - Chicago: Tue 24/03: £43
Go
Chicago - Orlando: Sat 4/04: £35
Go
Orlando - Portland: Mon 6/04: £139
Go
⌄
Chicago
&
Orlando
2 days
£224
8 days
Portland - Chicago: Sat 14/03: £43
Go
Chicago - Orlando: Mon 16/03: £42
Go
Orlando - Portland: Tue 24/03: £139
Go
⌄
Chicago
&
Orlando
3 days
£224
7 days
Portland - Chicago: Sat 14/03: £43
Go
Chicago - Orlando: Tue 17/03: £42
Go
Orlando - Portland: Tue 24/03: £139
Go
⌄
Chicago
&
Orlando
6 days
£224
9 days
Portland - Chicago: Wed 18/03: £43
Go
Chicago - Orlando: Tue 24/03: £42
Go
Orlando - Portland: Thu 2/04: £139
Go
⌄
Chicago
&
Orlando
5 days
£224
10 days
Portland - Chicago: Wed 18/03: £43
Go
Chicago - Orlando: Mon 23/03: £42
Go
Orlando - Portland: Thu 2/04: £139
Go
⌄
Chicago
&
Orlando
9 days
£228
5 days
Portland - Chicago: Thu 30/04: £43
Go
Chicago - Orlando: Sat 9/05: £17
Go
Orlando - Portland: Thu 14/05: £168
Go
⌄
Chicago
&
Orlando
10 days
£228
5 days
Portland - Chicago: Wed 29/04: £43
Go
Chicago - Orlando: Sat 9/05: £17
Go
Orlando - Portland: Thu 14/05: £168
Go
⌄
Chicago
&
Orlando
12 days
£244
3 days
Portland - Chicago: Wed 29/04: £43
Go
Chicago - Orlando: Mon 11/05: £33
Go
Orlando - Portland: Thu 14/05: £168
Go
⌄
Chicago
&
Orlando
9 days
£244
6 days
Portland - Chicago: Wed 29/04: £43
Go
Chicago - Orlando: Fri 8/05: £33
Go
Orlando - Portland: Thu 14/05: £168
Go
⌄
Chicago
&
Orlando
2 days
£244
12 days
Portland - Chicago: Thu 30/04: £43
Go
Chicago - Orlando: Sat 2/05: £33
Go
Orlando - Portland: Thu 14/05: £168
Go
⌄
Chicago
&
Orlando
3 days
£244
11 days
Portland - Chicago: Thu 30/04: £43
Go
Chicago - Orlando: Sun 3/05: £33
Go
Orlando - Portland: Thu 14/05: £168
Go
⌄
Chicago
&
Orlando
4 days
£244
10 days
Portland - Chicago: Thu 30/04: £43
Go
Chicago - Orlando: Mon 4/05: £33
Go
Orlando - Portland: Thu 14/05: £168
Go
⌄
Chicago
&
Orlando
8 days
£244
6 days
Portland - Chicago: Thu 30/04: £43
Go
Chicago - Orlando: Fri 8/05: £33
Go
Orlando - Portland: Thu 14/05: £168
Go
⌄
Chicago
&
Orlando
11 days
£244
4 days
Portland - Chicago: Wed 29/04: £43
Go
Chicago - Orlando: Sun 10/05: £33
Go
Orlando - Portland: Thu 14/05: £168
Go
⌄
Chicago
&
Orlando
5 days
£244
10 days
Portland - Chicago: Wed 29/04: £43
Go
Chicago - Orlando: Mon 4/05: £33
Go
Orlando - Portland: Thu 14/05: £168
Go
⌄
Chicago
&
Orlando
11 days
£244
3 days
Portland - Chicago: Thu 30/04: £43
Go
Chicago - Orlando: Mon 11/05: £33
Go
Orlando - Portland: Thu 14/05: £168
Go
⌄
Chicago
&
Orlando
3 days
£244
12 days
Portland - Chicago: Wed 29/04: £43
Go
Chicago - Orlando: Sat 2/05: £33
Go
Orlando - Portland: Thu 14/05: £168
Go
⌄
Chicago
&
Orlando
10 days
£244
4 days
Portland - Chicago: Thu 30/04: £43
Go
Chicago - Orlando: Sun 10/05: £33
Go
Orlando - Portland: Thu 14/05: £168
Go
⌄
Chicago
&
Orlando
4 days
£244
11 days
Portland - Chicago: Wed 29/04: £43
Go
Chicago - Orlando: Sun 3/05: £33
Go
Orlando - Portland: Thu 14/05: £168
Go
⌄
Chicago
&
Orlando
4 days
£252
6 days
Portland - Chicago: Sat 14/03: £43
Go
Chicago - Orlando: Wed 18/03: £70
Go
Orlando - Portland: Tue 24/03: £139
Go
⌄
Chicago
&
Orlando
3 days
£253
6 days
Portland - Chicago: Sat 14/03: £43
Go
Chicago - Orlando: Tue 17/03: £42
Go
Orlando - Portland: Mon 23/03: £168
Go
⌄
Chicago
&
Orlando
2 days
£253
7 days
Portland - Chicago: Sat 14/03: £43
Go
Chicago - Orlando: Mon 16/03: £42
Go
Orlando - Portland: Mon 23/03: £168
Go
⌄
Chicago
&
Orlando
9 days
£283
2 days
Portland - Chicago: Sat 14/03: £43
Go
Chicago - Orlando: Mon 23/03: £42
Go
Orlando - Portland: Wed 25/03: £198
Go
⌄
Chicago
&
Orlando
3 days
£283
8 days
Portland - Chicago: Sat 14/03: £43
Go
Chicago - Orlando: Tue 17/03: £42
Go
Orlando - Portland: Wed 25/03: £198
Go
⌄
Chicago
&
Orlando
2 days
£283
9 days
Portland - Chicago: Sat 14/03: £43
Go
Chicago - Orlando: Mon 16/03: £42
Go
Orlando - Portland: Wed 25/03: £198
Go
⌄
Chicago
&
Orlando
3 days
£283
2 days
Portland - Chicago: Sat 14/03: £43
Go
Chicago - Orlando: Tue 17/03: £42
Go
Orlando - Portland: Thu 19/03: £198
Go
⌄
Chicago
&
Orlando
2 days
£283
3 days
Portland - Chicago: Sat 14/03: £43
Go
Chicago - Orlando: Mon 16/03: £42
Go
Orlando - Portland: Thu 19/03: £198
Go
⌄