Chicago — Pay Half Price.
Chicago is a rail and air crossroads where O'Hare and Midway split the traffic. In our booking network Chicago pulls 55 inbound routes from 38 US cities, served by 4 airlines. Agent-negotiated fares start at $49 one-way, and travelers save up to 62% on this destination across the year.
Best Deals From
$49
Distance
55 routes
airports covered
4 airlines
Avg. Savings
up to 62%
Frequently Asked Questions
The cheapest way is to fly midweek (Tue/Wed) and book 15–45 days out through our agents to tap negotiated inventory. Deals to Chicago start around $49 one-way.
4 airlines serve Chicago across our tracked routes. Message us with your dates and we will quote the airline with the best fare for the exact flights you want.
For fares, January and February are the cheapest months; holiday weeks are the most expensive. Our agents match your dates to the off-peak window with the steepest discounts.