Category: Bookable Chicago

Icelandair has round-trip flights from Chicago (ORD) to Amsterdam, Copenhagen, or Frankfurt (AMS, CPH, FRA) for $385-$403 with a connection. Flights November to May. 

Note: A Carry on bag (20-lbs @ 21.6 x 15.7 x 7.8 inches) and a personal item (15.7 x 11.8 x 5.9 inches) is allowed for free on Icelandair. 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 Amsterdam, Copenhagen, or Frankfurt $385-$403 r/t – Icelandair

Airfare Deals Amsterdam Bookable Chicago Copenhagen Frankfurt From Chicago / Milwaukee IcelandAir

American Airlines has round-trip flights from Portland (PDX) to Chicago (ORD) for $217-$228, NONSTOP. Flights January to February. Departures on Monday, Tuesday, Wednesday, Thursday, and Saturday. 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: Portland to/from Chicago $217-$228 r/t – American

Airfare Deals American Airlines Bookable Chicago Bookable Deals Chicago From Chicago / Milwaukee From Seattle / Portland Portland

SAS has round-trip flights from Chicago (ORD) to Dublin (DUB) for $284-$290 with a connection. Flights February to March.

Note: Carry on bag with a maximum weight of 18 lbs is allowed for free on SAS. 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 Dublin $278-$290 r/t – SAS

Airfare Deals Bookable Chicago Bookable Deals Dublin From Chicago / Milwaukee SAS

Airfare Deals Bookable Chicago Bookable Deals From Chicago / Milwaukee Geneva SAS

Southwest has round-trip flights from Chicago (MDW) to Las Vegas (LAS) for $124, NONSTOP. $62 each-way. Flights in January and February. Origin/Destination reversible.

Note: You can save up to an additional $125 if you purchase your Flight+Hotel together as a package on Southwest Vacations and use the 125DOM19 coupon code. Before you commit, always compare the prices of the individual Flights and Hotel with other hotel booking sites like Hotels.com or Tripadvisor.

Read More Nonstop Flights: Chicago to/from Las Vegas $124 r/t – Southwest

Airfare Deals Bookable Chicago Bookable Deals From Chicago / Milwaukee Las Vegas Southwest

American Airlines has round-trip flights from Chicago (ORD) to Denver or Dallas (DEN/DFW) for $97, NONSTOP. Denver flights in November, January, and February. Dallas flights from October to April. Origin/Destination reversible. No Holidays. 

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 Denver or Dallas $97 r/t – American

Airfare Deals American Airlines Bookable Chicago Bookable Deals Dallas Denver From Chicago / Milwaukee Oneworld

United has round-trip flights from Chicago (ORD) to Orlando or San Diego (MCO/SAN) for $97-$139, NONSTOP. Flights October to February. No Holidays. Mostly on midweek, or weekdays.

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 (Orlando $97) or (San Diego $139) r/t – United

Airfare Deals Bookable Chicago Bookable Deals From Chicago / Milwaukee Orlando San Diego United

American Airlines, British Airways, and Delta have round-trip flights from Chicago (ORD) to London (LHR) for $374-$399, NONSTOP or with connections. Flights March, April, May, and August.

Note: Carry-on bag is allowed for free on American Airlines, British Airways, and 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: Chicago to London $374-$399 r/t – American / British Airways / Delta

Airfare Deals American Airlines Bookable Chicago Bookable Deals British Delta From Chicago / Milwaukee London Oneworld SkyTeam Star Alliance United

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Southwest has round-trip flights from Chicago (MDW) to Houston, Austin, New Orleans, Atlanta, Tampa, or Baltimore (HOU, AUS, MSY, ATL, TPA, BWI) for $108, NONSTOP. $54 each-way. Flights between October and March. Origin/Destination reversible.

Note: You can save up to an additional $125 if you purchase your Flight+Hotel together as a package on Southwest Vacations and use the 125DOM19 coupon code.

Read More Nonstop Flights: Chicago to/from Houston, Austin, New Orleans, Atlanta, Tampa, or Baltimore $108 r/t – Southwest

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American Airlines has round-trip flights from Chicago (ORD) to Sao Paulo (GRU) for $545 with a connection. Flights in November, March, and April.

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.

We don’t charge a subscription fee. All of our deal notifications are available for FREE via Instagram, Facebook, Twitter, our Webpage, and our E-mail list. If you are paying someone a subscription fee for our content, you are being ripped off.

Read More Cheap Flights: Chicago to Sao Paulo $545 r/t – American

Airfare Deals American Airlines Bookable Chicago Bookable Deals From Chicago / Milwaukee Oneworld Sao Paulo