Category: From Chicago / Milwaukee

American Airlines has round-trip flights from Chicago (ORD) to Montreal or Toronto (YUL, YYZ) for $172-$177, NONSTOP. Montreal flights in November, January, February, and March. Toronto flights from November and September. Origin/Destination reversible.

Note: Carry-on bag is allowed for free on American Airlines. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

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Read More Nonstop Flights: Chicago to/from Montreal or Toronto $172-$177 r/t – American

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United has round-trip flights from Chicago (ORD) to Cancun (CUN) for $180-$182, NONSTOP. Flights January to March. Departures on Monday, Tuesday, and Sunday. Origin/Destination reversible.

Note: United “Basic Economy” fares do not include a free carry-on bag. Only a personal item (like a small laptop bag) is free. Seats are randomly assigned for free prior to boarding. If you have the United MileagePlus credit-card, use the “free checked bag” perk.

Note: The personal item size on United flights is smaller (9-in/10-in/17-in) than Frontier or Spirit (8-in/14-in/18-in).

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Read More Nonstop Flights: Chicago to/from Cancun $180-$182 r/t – United Basic Economy

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COPA has round-trip flights from Chicago (ORD) to Santo Domingo (SDQ) for $324 with a connection.  Flights March to May. Extended Weekends available.

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Read More Cheap Flights: Chicago to Santo Domingo $324 r/t – COPA

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COPA has round-trip flights from Chicago or Los Angeles (ORD/LAX) to Quito (UIO) for $387-$401 with a connection. Flights December to May. Extended Weekends available.

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Read More Cheap Flights: Chicago or Los Angeles to Quito $387-$401 r/t – COPA

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American Airlines has round-trip flights from Chicago (ORD) to Calgary (YYC) for $163, NONSTOP. Flights November to January. Extended Weekends available. Origin/Destination reversible.

Note: Carry-on bag is allowed for free on American Airlines. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

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Read More Nonstop Flights: Chicago to/from Calgary $163 r/t – American

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[11/13/2019 @ 2:41 PM CT] Matched by AA. SkyTeam fares were removed.

Air France has round-trip flights from Chicago (ORD) to Paris (CDG) for $283, NONSTOP. Flights in May, August, and September. Departures on Monday, Tuesday, Wednesday, and Sunday.

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Read More Nonstop Flights: Chicago to Paris $283 r/t – Air France / Delta

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American Airlines has round-trip flights from Chicago (ORD) to Dallas, Atlanta, or Minneapolis (DFW, ATL, MSP) for $87-$101, NONSTOP. Flights November to May.

Note: Carry-on bag is allowed for free on American Airlines. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

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Read More Nonstop Flights: Chicago to/from Dallas, Atlanta, or Minneapolis $87-$101 r/t – American

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American Airlines has round-trip flights from Chicago (ORD) to Miami, Jacksonville, or Fort Lauderdale (MIA, JAX, FLL) for $87-$128, NONSTOP. Flights January to March. No Holidays. Mostly midweek. Origin/Destination reversible.

Note: Carry-on bag is allowed for free on American Airlines. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

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Read More Nonstop Flights: Chicago to/from Miami, Jacksonville, or Fort Lauderdale $87-$128 r/t – American

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Delta has round-trip flights from Seattle (SEA) to Chicago (ORD) for $157-$165, NONSTOP. Flights December to March. Extended Weekends available. No Holidays. Origin/Destination reversible.

Note: Carry-on bag is allowed for free on Delta. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

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Read More Nonstop Flights: Seattle to/from Chicago $157-$165 r/t – Delta

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Tap Air Portugal has round-trip flights from Chicago (ORD) to Tenerife (TFS) for $442-$508 with a connection. Flights January, February, April, June, July, August, and September.

Note: Requires an overnight connection in Lisbon on the return.

Note: Carry on bag with a maximum weight of 17.6 lbs is allowed for free on TAP. You can avoid seat selection fees by accepting the randomly assigned seat at the gate.

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Read More Cheap Flights: Chicago to/from Tenerife, Canary Islands $442-$508 r/t – Tap Air Portugal

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