Award Flights from Chicago — All Airports

22,700 award deals from Chicago across all cabin classes and loyalty programs. Scores updated daily. Prices from 16,000 points.

Airports in this area
ORDMDW

Economy

Chicago → Madrid
iberia
32,000 pts
100/100
Chicago → Dublin
Alaska Mileage Plan
50,000 pts
94/100
Chicago → London
Alaska Mileage Plan
22,500 pts
91/100
Chicago → Paris
Alaska Mileage Plan
22,500 pts
91/100
Chicago → Paris
Alaska Mileage Plan
45,000 pts
91/100
Chicago → Madrid
iberia
16,000 pts
90/100
Chicago → Rome
American AAdvantage
48,500 pts
90/100
Chicago → Tokyo
Alaska Mileage Plan
75,000 pts
87/100
Chicago → Tokyo
Alaska Mileage Plan
77,500 pts
87/100
Chicago → Seoul
Alaska Mileage Plan
79,500 pts
87/100
Chicago → Rome
American AAdvantage
21,000 pts
86/100
Chicago → Zurich
United MileagePlus
52,418 pts
86/100
Chicago → London
American AAdvantage
42,000 pts
85/100
Chicago → Barcelona
American AAdvantage
47,500 pts
83/100
Chicago → Dublin
Alaska Mileage Plan
27,500 pts
82/100
Chicago → Tokyo
Alaska Mileage Plan
37,500 pts
82/100
Chicago → Tokyo
Alaska Mileage Plan
40,000 pts
82/100
Chicago → Seoul
Alaska Mileage Plan
40,000 pts
82/100

Premium Economy

Chicago → Madrid
Alaska Mileage Plan
35,000 pts
100/100
Chicago → Paris
Alaska Mileage Plan
35,000 pts
100/100
Chicago → Tokyo
Alaska Mileage Plan
50,000 pts
100/100
Chicago → Tokyo
Alaska Mileage Plan
50,000 pts
100/100
Chicago → Madrid
Alaska Mileage Plan
70,000 pts
100/100
Chicago → Tokyo
Alaska Mileage Plan
100,000 pts
100/100
Chicago → Dublin
United MileagePlus
100,000 pts
100/100
Chicago → Amsterdam
United MileagePlus
100,000 pts
100/100
Chicago → Rome
Alaska Mileage Plan
70,000 pts
99/100
Chicago → Paris
Alaska Mileage Plan
70,000 pts
96/100
Chicago → Rome
Alaska Mileage Plan
35,000 pts
95/100
Chicago → Zurich
United MileagePlus
100,000 pts
92/100
Chicago → Dublin
Alaska Mileage Plan
35,000 pts
90/100
Chicago → London
United MileagePlus
50,000 pts
90/100
Chicago → Amsterdam
United MileagePlus
50,000 pts
90/100
Chicago → Tokyo
Alaska Mileage Plan
100,000 pts
90/100
Chicago → Zurich
United MileagePlus
50,000 pts
88/100
Chicago → Hong Kong
Alaska Mileage Plan
110,000 pts
86/100
Chicago → Barcelona
Alaska Mileage Plan
70,000 pts
85/100

First

Chicago → Rome
Alaska Mileage Plan
165,000 pts
100/100
Chicago → Barcelona
Alaska Mileage Plan
165,000 pts
100/100
Chicago → London
Alaska Mileage Plan
170,500 pts
100/100
Chicago → Delhi
Air Canada Aeroplan
260,000 pts
100/100
Chicago → Paris
Alaska Mileage Plan
135,000 pts
98/100
Chicago → Dublin
Alaska Mileage Plan
67,500 pts
94/100
Chicago → Paris
Alaska Mileage Plan
67,500 pts
94/100
Chicago → Delhi
Air Canada Aeroplan
150,000 pts
91/100
Chicago → Rome
Alaska Mileage Plan
82,500 pts
86/100
Chicago → Madrid
Alaska Mileage Plan
82,500 pts
85/100
Chicago → London
Alaska Mileage Plan
82,500 pts
85/100
Chicago → Athens
Alaska Mileage Plan
165,000 pts
85/100

Business

Chicago → Paris
Air Canada Aeroplan
70,000 pts
99/100
Chicago → London
Air Canada Aeroplan
70,000 pts
98/100
Chicago → Rome
Air Canada Aeroplan
140,000 pts
98/100
Chicago → Dublin
United MileagePlus
148,000 pts
98/100
Chicago → Zurich
Air Canada Aeroplan
145,000 pts
95/100
Chicago → Madrid
iberia
81,000 pts
93/100
Chicago → Madrid
Alaska Mileage Plan
55,000 pts
92/100
Chicago → Tokyo
Air Canada Aeroplan
87,500 pts
92/100
Chicago → Seoul
Air Canada Aeroplan
87,500 pts
92/100
Chicago → Paris
Air Canada Aeroplan
125,000 pts
92/100
Chicago → Tokyo
Air Canada Aeroplan
87,500 pts
91/100
Chicago → Tokyo
Air Canada Aeroplan
175,000 pts
91/100
Chicago → Seoul
Air Canada Aeroplan
175,000 pts
91/100
Chicago → Rome
Air Canada Aeroplan
70,000 pts
90/100
Chicago → Dublin
United MileagePlus
93,000 pts
90/100
Chicago → Amsterdam
Air Canada Aeroplan
70,000 pts
89/100
Chicago → Delhi
United MileagePlus
176,000 pts
89/100
Chicago → Amsterdam
Air Canada Aeroplan
185,000 pts
89/100
Chicago → Shanghai
Air Canada Aeroplan
87,500 pts
87/100
Chicago → London
Air Canada Aeroplan
150,000 pts
87/100
Chicago → Beijing
Air Canada Aeroplan
175,000 pts
87/100
Chicago → Lisbon
Air Canada Aeroplan
130,000 pts
86/100
Chicago → Warsaw
Air Canada Aeroplan
140,000 pts
86/100
Chicago → Tokyo
United MileagePlus
185,000 pts
86/100
Chicago → Copenhagen
Air Canada Aeroplan
140,000 pts
85/100
Chicago → Barcelona
American AAdvantage
149,500 pts
85/100
Chicago → Zurich
Air Canada Aeroplan
75,000 pts
84/100
Chicago → Frankfurt
Air Canada Aeroplan
75,000 pts
84/100
Chicago → Beijing
Air Canada Aeroplan
87,500 pts
84/100
Chicago → Warsaw
Air Canada Aeroplan
70,000 pts
83/100
Chicago → Lisbon
Air Canada Aeroplan
60,000 pts
82/100
Top programs from Chicago
Alaska Mileage PlanAir Canada AeroplanUnited MileagePlusqantasFlying BlueVirgin Australia Velocity
Top destinations
To LondonTo RomeTo ParisTo DublinTo BarcelonaTo CopenhagenTo AmsterdamTo MadridTo AthensTo Reykjavik