Cheap Flights from Chicago ORD in 2026
Looking for cheap flights from Chicago? We monitor ORD and MDW 24/7, sending you deals when prices drop. Our Chicago members saved an average of $$400 on flights last year. Join 1261 other Chicago travelers getting exclusive deals.
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Updated March 12, 2026 — Deals from Chicago available now. Prices can change anytime.
Paris
France
Save $589
London
UK
Save $587
Cancun
Mexico
Save $276
Hover to see more deals
Cancun
Mexico
Save $276
London
UK
Save $587
Paris
France
Save $589
Real examples
Recent deals our members from Chicago received
These are actual deals we sent to our Chicago members. Deals like these go out every week.
Paris
France
Save $589
London
UK
Save $587
Cancun
Mexico
Save $276
Tokyo
Japan
Save $785
Rome
Italy
Save $643
New deals added weekly. Join to never miss one.
Popular Routes from Chicago
ORD → DUB
Dublin
Deals from $399
ORD → LHR
London
Deals from $429
ORD → CUN
Cancun
Deals from $259
ORD → FCO
Rome
Deals from $489
Prices shown are typical deal prices we've found. Actual prices vary.
About Cheap Flights from Chicago ORD
O'Hare (ORD) is the 6th busiest airport globally, serving as a major United and American hub with nonstops to 60+ countries. Midway (MDW) is Southwest's stronghold with excellent domestic and Caribbean deals. We monitor both because Midway often beats O'Hare by $50-100 on leisure routes like Cancun, while O'Hare dominates for international.
Popular Destinations from Chicago
The most popular flight deals from Chicago include routes to Dublin, London, Tokyo, Cancun, Rome. We see the best prices during January-March and October-November.
Airlines Operating from ORD
Major carriers at ORD include United, American, Southwest, Spirit, Aer Lingus. We monitor all airlines for deals, including mistake fares and flash sales that typically last only hours.
Average savings: Homebase Flights subscribers from Chicago save an average of $400 per booked trip. One deal typically saves you $420+ - that's 70 months of membership at $5.99/month.
Flight data sourced from Google Flights API and updated daily.
Simple process
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Loved by travelers everywhere
Join thousands who are saving big on every trip
I saved $800 on a round-trip flight from Chicago. This service pays for itself on the first deal!
Sarah M.
Chicago
Best travel investment I've made. Found a $300 flight to Paris that normally costs over $1,000.
Michael R.
Chicago
The deals are insane. I've taken 4 international trips this year that I never thought I could afford.
Jessica L.
Chicago
Frequently Asked Questions
Common questions about flights from Chicago
Which Chicago airport is cheaper — O'Hare or Midway?
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