$280 Cheap Flights from Madison (MSN) to Chicago (MDW)

Cheap Flights from Madison (MSN) to Chicago (MDW) start at $280 for one-way and $389 for round trip. Earn your airline miles on top of our rewards!

$280
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$280 Cheap Flights From Madison (MSN) To Chicago (MDW)

2 weeks from now

Cheap Flights from Madison (MSN) to Chicago (MDW) start at $280 for one-way and $389 for round trip. Earn your airline miles on top of our rewards!

expedia.com

$297
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Flights From Madison To Chicago (MSN To MDW) - Travelocity

2 weeks from now

$297 Search for cheap flights deals from MSN to MDW (Dane County Regional to Midway Intl.). We offer cheap direct, non-stop flights including one way and roundtrip tickets.

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Cheap Flights From Madison To Chicago Midway Airport From $473 …

2 weeks from now

Search and compare airfare from 1000+ airlines and travel sites to get the cheapest flights from Madison to Chicago Midway Airport with momondo.

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$125 Cheap Flights From Madison To Chicago In 2025 | Momondo

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Search and compare airfare from 1000+ airlines and travel sites to get the cheapest flights from Madison to Chicago with momondo.

momondo.com

$117
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$117+ Flights From Madison To Chicago | Cheapflights

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Find airfare and ticket deals for cheap flights from Madison to Chicago. Search flight deals from various travel partners with one click at $117.

cheapflights.com

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Cheap Flights From Madison (MSN) To Chicago (CHI) - Tripadvisor

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Up to 3% cash back · Book Cheap Flights from Madison to Chicago: Search and compare airfares on Tripadvisor to find the best flights for your trip to Chicago. Choose the best airline …

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$228 Cheap Flights From Chicago (MDW) To Madison (MSN)

2 weeks from now

Cheap Flights from Chicago (MDW) to Madison (MSN) start at $228 for one-way and $443 for round trip. Earn your airline miles on top of our rewards!

expedia.com

3%
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Cheap Flights From Madison, WI To Chicago, IL - Kiwi.com

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Up to 3% cash back · Search, compare, and book flights to travel from Madison, WI to Chicago, IL. Cheap, quick, and easy ways to explore any destination.

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$309RT! Cheap Flights From Madison, WI (MSN) To Chicago, IL …

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Best site for finding today’s lowest flight prices, unadvertised fare sales, and mistake prices. Updated daily. Find the best price before you book your trip to Chicago, IL (ORD).

airfarewatchdog.com