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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.

San Francisco from £596? Yes, from London
🇬🇧From London

San Francisco from £596? Yes, from London

Direct flights to the US West Coast from under £600 return, plus Business Class deals to New York and LA - and 22 premium cabin deals unlocked for subscribers.

Jun 6
Boston to Tel Aviv for $1518?$1518
🇺🇸From Boston

Boston to Tel Aviv for $1518?

That BOS-TLV fare is 58% below its typical median price - plus direct flights to Rome from $665 and Nassau from $371 are turning heads this week.

Jun 5
UK Regional Airports to Budapest for £97?

UK Regional Airports to Budapest for £97?

Manchester to Budapest is 74% below typical right now at just £97 return - plus direct flights to Berlin for £50 and Copenhagen for £40 from MAN.

Jun 5
Los Angeles from £572? Yes, from London
🇬🇧From London

Los Angeles from £572? Yes, from London

This week: direct flights to LA from £572, New York from £623, San Francisco from £588 - plus premium cabin deals for subscribers. Save up to 25% vs typical prices.

May 30
New York to Tel Aviv for $2614?$2614
🇺🇸From New York

New York to Tel Aviv for $2614?

JFK to Tel Aviv is 37% below its typical price this week - plus direct flights to Cancun from Newark under $400 and a Dubai deal flying Emirates nonstop.

May 29
57% off Washington DC → Paris ($1048)$1048
🇺🇸From Washington DC

57% off Washington DC → Paris ($1048)

Paris for $1048 round-trip from Dulles - 57% below the typical median price - plus direct flights to London from $880 and Frankfurt from $1234. Summer Europe deals are here.

May 29

Want more deals like these?

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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