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Cheap Flights to Chicago

Two major airports and brutal competition keep Chicago fares low

Flight Deals to Chicago

Chicago is served by O'Hare (ORD) — a massive United and American hub — and Midway (MDW), a Southwest stronghold. That dual-airport setup creates relentless competition, so domestic fares into Chicago stay among the lowest of any major US city. Frontier and Spirit add ultra-low-cost options at O'Hare, meaning a deal is almost always available if you're willing to compare both airports.

Best Time to Fly to Chicago

January through March (embrace the cold) and late August through October offer the cheapest fares. Avoid summer festival season and the December holidays.

This Week's Picks

See What You're Missing

Real deals from this week - subscribers get these and more, every Friday.

£471 London to San Francisco + 14 more deals
🇬🇧From London

£471 London to San Francisco + 14 more deals

This week: direct flights to San Francisco from £471, Barcelona from £65, Singapore from £659, and Business Class deals unlocked for Premium members. Up to 56% below typical prices.

Oct 10
77% off San Francisco → Las Vegas ($38)$38
🇺🇸From San Francisco

77% off San Francisco → Las Vegas ($38)

OAK → Las Vegas for just $38 round-trip - 77% below the typical $164 median - plus SFO → Cancun for $335 (75% off) and SFO → Tokyo for $708.

Oct 9
77% off Los Angeles → Seattle ($38)$38
🇺🇸From Los Angeles

77% off Los Angeles → Seattle ($38)

LAX to Seattle for just $38 round-trip - 77% below the typical $165 median - plus Tokyo Narita for $663 (64% off) and Los Cabos for $340 (50% off) direct from LAX.

Oct 9

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Tips for Finding Cheap Flights to Chicago

Fly to Chicago From

🇺🇸New York→🇺🇸Los Angeles→🇺🇸San Francisco→🇺🇸Atlanta→🇺🇸Miami→🇺🇸Washington DC→🇺🇸Dallas→🇺🇸Seattle→

Other Popular Destinations

🎬Flights to Los Angeles→⭐Flights to Dallas→☕Flights to Seattle→🏖️Flights to San Diego→🎷Flights to New Orleans→⛱️Flights to Fort Lauderdale→

Frequently Asked Questions

Is it cheaper to fly into O'Hare or Midway?

It varies by route. Midway (MDW) is often cheaper if Southwest serves your origin, while O'Hare (ORD) wins on routes where United, American, Spirit, and Frontier compete head-to-head. Comparing both airports is the single best way to save on Chicago flights.

When are flights to Chicago cheapest?

January through March is the cheapest window — winter weather suppresses leisure demand and roundtrip fares from the coasts can drop to $120-180. Late summer and early fall also see dips. Summer festivals and the December holidays bring the highest prices.

Which airlines fly cheapest to Chicago?

Southwest dominates Midway with competitive fares and free bags, while Spirit and Frontier offer the lowest base prices at O'Hare. United and American also compete heavily at ORD, so even full-service fares remain affordable thanks to the city's two-airport rivalry.

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