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Chicago & Orlando

from Portland

Best deal: £257

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
5 days
£257
3 days
Portland - Chicago: Mon 16/02: £81
Go
Chicago - Orlando: Sat 21/02: £27
Go
Orlando - Portland: Tue 24/02: £149
Go
⌄
Chicago
&
Orlando
2 days
£262
6 days
Portland - Chicago: Mon 16/02: £81
Go
Chicago - Orlando: Wed 18/02: £32
Go
Orlando - Portland: Tue 24/02: £149
Go
⌄
Chicago
&
Orlando
3 days
£273
5 days
Portland - Chicago: Mon 16/02: £81
Go
Chicago - Orlando: Thu 19/02: £43
Go
Orlando - Portland: Tue 24/02: £149
Go
⌄
Chicago
&
Orlando
4 days
£273
4 days
Portland - Chicago: Mon 16/02: £81
Go
Chicago - Orlando: Fri 20/02: £43
Go
Orlando - Portland: Tue 24/02: £149
Go
⌄
Chicago
&
Orlando
6 days
£273
2 days
Portland - Chicago: Mon 16/02: £81
Go
Chicago - Orlando: Sun 22/02: £43
Go
Orlando - Portland: Tue 24/02: £149
Go
⌄
Chicago
&
Orlando
12 days
£273
3 days
Portland - Chicago: Thu 19/03: £81
Go
Chicago - Orlando: Tue 31/03: £43
Go
Orlando - Portland: Fri 3/04: £149
Go
⌄
Chicago
&
Orlando
4 days
£273
11 days
Portland - Chicago: Thu 19/03: £81
Go
Chicago - Orlando: Mon 23/03: £43
Go
Orlando - Portland: Fri 3/04: £149
Go
⌄
Chicago
&
Orlando
12 days
£273
2 days
Portland - Chicago: Thu 19/03: £81
Go
Chicago - Orlando: Tue 31/03: £43
Go
Orlando - Portland: Thu 2/04: £149
Go
⌄
Chicago
&
Orlando
4 days
£273
10 days
Portland - Chicago: Thu 19/03: £81
Go
Chicago - Orlando: Mon 23/03: £43
Go
Orlando - Portland: Thu 2/04: £149
Go
⌄
Chicago
&
Orlando
4 days
£273
2 days
Portland - Chicago: Thu 19/03: £81
Go
Chicago - Orlando: Mon 23/03: £43
Go
Orlando - Portland: Wed 25/03: £149
Go
⌄
Chicago
&
Orlando
5 days
£279
4 days
Portland - Chicago: Mon 16/02: £81
Go
Chicago - Orlando: Sat 21/02: £27
Go
Orlando - Portland: Wed 25/02: £171
Go
⌄
Chicago
&
Orlando
2 days
£284
7 days
Portland - Chicago: Mon 16/02: £81
Go
Chicago - Orlando: Wed 18/02: £32
Go
Orlando - Portland: Wed 25/02: £171
Go
⌄
Chicago
&
Orlando
13 days
£286
2 days
Portland - Chicago: Thu 19/03: £81
Go
Chicago - Orlando: Wed 1/04: £56
Go
Orlando - Portland: Fri 3/04: £149
Go
⌄
Chicago
&
Orlando
6 days
£286
9 days
Portland - Chicago: Thu 19/03: £81
Go
Chicago - Orlando: Wed 25/03: £56
Go
Orlando - Portland: Fri 3/04: £149
Go
⌄
Chicago
&
Orlando
6 days
£286
8 days
Portland - Chicago: Thu 19/03: £81
Go
Chicago - Orlando: Wed 25/03: £56
Go
Orlando - Portland: Thu 2/04: £149
Go
⌄
Chicago
&
Orlando
5 days
£289
10 days
Portland - Chicago: Thu 19/03: £81
Go
Chicago - Orlando: Tue 24/03: £59
Go
Orlando - Portland: Fri 3/04: £149
Go
⌄
Chicago
&
Orlando
5 days
£289
9 days
Portland - Chicago: Thu 19/03: £81
Go
Chicago - Orlando: Tue 24/03: £59
Go
Orlando - Portland: Thu 2/04: £149
Go
⌄
Chicago
&
Orlando
7 days
£295
2 days
Portland - Chicago: Mon 16/02: £81
Go
Chicago - Orlando: Mon 23/02: £43
Go
Orlando - Portland: Wed 25/02: £171
Go
⌄
Chicago
&
Orlando
6 days
£295
3 days
Portland - Chicago: Mon 16/02: £81
Go
Chicago - Orlando: Sun 22/02: £43
Go
Orlando - Portland: Wed 25/02: £171
Go
⌄
Chicago
&
Orlando
4 days
£295
5 days
Portland - Chicago: Mon 16/02: £81
Go
Chicago - Orlando: Fri 20/02: £43
Go
Orlando - Portland: Wed 25/02: £171
Go
⌄
Chicago
&
Orlando
3 days
£295
6 days
Portland - Chicago: Mon 16/02: £81
Go
Chicago - Orlando: Thu 19/02: £43
Go
Orlando - Portland: Wed 25/02: £171
Go
⌄
Chicago
&
Orlando
5 days
£316
10 days
Portland - Chicago: Mon 16/02: £81
Go
Chicago - Orlando: Sat 21/02: £27
Go
Orlando - Portland: Tue 3/03: £208
Go
⌄
Chicago
&
Orlando
5 days
£316
5 days
Portland - Chicago: Mon 16/02: £81
Go
Chicago - Orlando: Sat 21/02: £27
Go
Orlando - Portland: Thu 26/02: £208
Go
⌄
Chicago
&
Orlando
8 days
£316
7 days
Portland - Chicago: Mon 16/02: £81
Go
Chicago - Orlando: Tue 24/02: £27
Go
Orlando - Portland: Tue 3/03: £208
Go
⌄
Chicago
&
Orlando
9 days
£316
6 days
Portland - Chicago: Mon 16/02: £81
Go
Chicago - Orlando: Wed 25/02: £27
Go
Orlando - Portland: Tue 3/03: £208
Go
⌄
Chicago
&
Orlando
8 days
£316
2 days
Portland - Chicago: Mon 16/02: £81
Go
Chicago - Orlando: Tue 24/02: £27
Go
Orlando - Portland: Thu 26/02: £208
Go
⌄
Chicago
&
Orlando
12 days
£316
3 days
Portland - Chicago: Mon 16/02: £81
Go
Chicago - Orlando: Sat 28/02: £27
Go
Orlando - Portland: Tue 3/03: £208
Go
⌄
Chicago
&
Orlando
2 days
£321
13 days
Portland - Chicago: Mon 16/02: £81
Go
Chicago - Orlando: Wed 18/02: £32
Go
Orlando - Portland: Tue 3/03: £208
Go
⌄
Chicago
&
Orlando
2 days
£321
8 days
Portland - Chicago: Mon 16/02: £81
Go
Chicago - Orlando: Wed 18/02: £32
Go
Orlando - Portland: Thu 26/02: £208
Go
⌄
Chicago
&
Orlando
3 days
£322
11 days
Portland - Chicago: Fri 20/03: £130
Go
Chicago - Orlando: Mon 23/03: £43
Go
Orlando - Portland: Fri 3/04: £149
Go
⌄
Chicago
&
Orlando
3 days
£322
10 days
Portland - Chicago: Fri 20/03: £130
Go
Chicago - Orlando: Mon 23/03: £43
Go
Orlando - Portland: Thu 2/04: £149
Go
⌄
Chicago
&
Orlando
3 days
£322
2 days
Portland - Chicago: Fri 20/03: £130
Go
Chicago - Orlando: Mon 23/03: £43
Go
Orlando - Portland: Wed 25/03: £149
Go
⌄
Chicago
&
Orlando
11 days
£322
3 days
Portland - Chicago: Fri 20/03: £130
Go
Chicago - Orlando: Tue 31/03: £43
Go
Orlando - Portland: Fri 3/04: £149
Go
⌄
Chicago
&
Orlando
11 days
£322
2 days
Portland - Chicago: Fri 20/03: £130
Go
Chicago - Orlando: Tue 31/03: £43
Go
Orlando - Portland: Thu 2/04: £149
Go
⌄
Chicago
&
Orlando
10 days
£333
2 days
Portland - Chicago: Sat 21/03: £141
Go
Chicago - Orlando: Tue 31/03: £43
Go
Orlando - Portland: Thu 2/04: £149
Go
⌄
Chicago
&
Orlando
2 days
£333
11 days
Portland - Chicago: Sat 21/03: £141
Go
Chicago - Orlando: Mon 23/03: £43
Go
Orlando - Portland: Fri 3/04: £149
Go
⌄
Chicago
&
Orlando
10 days
£333
3 days
Portland - Chicago: Sat 21/03: £141
Go
Chicago - Orlando: Tue 31/03: £43
Go
Orlando - Portland: Fri 3/04: £149
Go
⌄
Chicago
&
Orlando
2 days
£333
2 days
Portland - Chicago: Sat 21/03: £141
Go
Chicago - Orlando: Mon 23/03: £43
Go
Orlando - Portland: Wed 25/03: £149
Go
⌄
Chicago
&
Orlando
2 days
£333
10 days
Portland - Chicago: Sat 21/03: £141
Go
Chicago - Orlando: Mon 23/03: £43
Go
Orlando - Portland: Thu 2/04: £149
Go
⌄
Chicago
&
Orlando
5 days
£335
9 days
Portland - Chicago: Fri 20/03: £130
Go
Chicago - Orlando: Wed 25/03: £56
Go
Orlando - Portland: Fri 3/04: £149
Go
⌄
Chicago
&
Orlando
5 days
£335
8 days
Portland - Chicago: Fri 20/03: £130
Go
Chicago - Orlando: Wed 25/03: £56
Go
Orlando - Portland: Thu 2/04: £149
Go
⌄
Chicago
&
Orlando
12 days
£335
2 days
Portland - Chicago: Fri 20/03: £130
Go
Chicago - Orlando: Wed 1/04: £56
Go
Orlando - Portland: Fri 3/04: £149
Go
⌄
Chicago
&
Orlando
4 days
£338
10 days
Portland - Chicago: Fri 20/03: £130
Go
Chicago - Orlando: Tue 24/03: £59
Go
Orlando - Portland: Fri 3/04: £149
Go
⌄
Chicago
&
Orlando
4 days
£338
9 days
Portland - Chicago: Fri 20/03: £130
Go
Chicago - Orlando: Tue 24/03: £59
Go
Orlando - Portland: Thu 2/04: £149
Go
⌄
Chicago
&
Orlando
13 days
£344
2 days
Portland - Chicago: Fri 20/03: £130
Go
Chicago - Orlando: Thu 2/04: £43
Go
Orlando - Portland: Sat 4/04: £171
Go
⌄
Chicago
&
Orlando
11 days
£344
4 days
Portland - Chicago: Fri 20/03: £130
Go
Chicago - Orlando: Tue 31/03: £43
Go
Orlando - Portland: Sat 4/04: £171
Go
⌄
Chicago
&
Orlando
3 days
£344
12 days
Portland - Chicago: Fri 20/03: £130
Go
Chicago - Orlando: Mon 23/03: £43
Go
Orlando - Portland: Sat 4/04: £171
Go
⌄
Chicago
&
Orlando
11 days
£346
2 days
Portland - Chicago: Sat 21/03: £141
Go
Chicago - Orlando: Wed 1/04: £56
Go
Orlando - Portland: Fri 3/04: £149
Go
⌄
Chicago
&
Orlando
4 days
£346
8 days
Portland - Chicago: Sat 21/03: £141
Go
Chicago - Orlando: Wed 25/03: £56
Go
Orlando - Portland: Thu 2/04: £149
Go
⌄
Chicago
&
Orlando
4 days
£346
9 days
Portland - Chicago: Sat 21/03: £141
Go
Chicago - Orlando: Wed 25/03: £56
Go
Orlando - Portland: Fri 3/04: £149
Go
⌄

... 8 more possible dates exist ...