Category: Bookable Chicago

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KLM and Air France have have round-trip flights from Chicago (ORD) to Frankfurt or Munich (FRA/MUC) starting at $354 with a connection. Flights mid-November to mid-May. Holiday Blackouts apply. Expect prices to fluctuate by about +/- $10. Flight may operate as a Delta code-share. 7-day minimum stay required.

Note: Carry-on bag is allowed for free, but a checked-bag will have a +$60 fee each-way.

Read More Cheap Flights: Chicago to Frankfurt or Munich $354-$365 r/t – KLM / Air France / Delta

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American Airlines and Oneworld partners have round-trip flights from Chicago (ORD) to Madrid (MAD) starting at $429, NONSTOP. Flights November to May. Holiday blackouts apply. 8-day minimum stay required.

Note: Fare allows for a free carry-on bag, but checked bags will cost +$60 each-way. If you’re checking a bag, it may be a better option to upgrade into “Regular Economy” for +$45 each-way for the included checked bag.

Read More Nonstop Flights: Chicago to Madrid $429 r/t – American

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Southwest has round-trip flights from Chicago (MDW) to Houston or Dallas (HOU/DAL) for $90, NONSTOP. $45 each-way. Flights from November to February. Origin/Destination reversible.

Note: Southwest doesn’t charge a change fee or a cancellation fee and allows for 2 checked bags for free.

Note: You may find additional savings by booking your Flight+Hotel together as a package on Southwest Vacations.

Read More Nonstop Flights: Chicago to/from Houston or Dallas $90 r/t – Southwest

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KLM, Air France, and SkyTeam partners have round-trip flights from Chicago (ORD) to Madrid (MAD) for $358-$388 with a connection. Flights from November to May. 7-day minimum stay required. Christmas Blackout. Expect prices to fluctuate by +/- $15. Flight may operate as a Delta/SkyTeam code-share.

Note: Carry-on bag is allowed for free, but it will cost +$60 more each-way to check a bag.

Read More Cheap Flights: Chicago to Madrid $358-$388 r/t – Delta + SkyTeam

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