Category: Bookable Chicago

Spirit has round-trip flights from Chicago (ORD) to Cancun (CUN) for $190-$199, NONSTOP. Flights in September and November. Origin/Destination reversible.

Note: Spirit fares do not include a free carry-on bag. Only a small personal item, like a Jansport City Scout backpack is free. You can avoid paying for seat selection if you accept the randomly assigned seat prior to boarding.

Note: Spirit seats only have 28-inches of pitch; 2-to-3 inches less space than most other airlines.

Read More Nonstop Flights: Chicago to/from Cancun $190-$199 r/t – Spirit

Airfare Deals Bookable Chicago Bookable Deals Cancun From Chicago / Milwaukee Spirit

Airfare Deals Bologna Bookable Chicago Bookable Deals Delta From Chicago / Milwaukee KLM SkyTeam

British Airways, Iberia, American Airlines, Lufthansa, and various other airlines have round-trip flights from Chicago (ORD) to Bologna (BLQ) for $468-$490 with a connection. Flights October to March. Departures on Tuesday and Wednesday. 7-day minimum stay required.

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

Read More Cheap Flights: Chicago to Bologna, Italy $468-$490 r/t – British Airways / Iberia / American / Lufthansa

Airfare Deals American Airlines Bologna Bookable Chicago Bookable Deals British From Chicago / Milwaukee Iberia Lufthansa Oneworld Star Alliance

Airfare Deals Belize City Bookable Chicago Bookable Deals Delta From Chicago / Milwaukee SkyTeam

[08/08/2019 @ 01:19 PM CT] Post updated. Now Jan-Apr. Was Jan-Feb.

American Airlines has round-trip flights from Chicago (ORD) to Los Angeles (LAX) for $113, NONSTOP. Flights January to April. A few 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.

Read More Nonstop Flights: Chicago to/from Los Angeles $113 r/t – American

Administrative American Airlines Bookable Chicago Bookable Deals Bookable LAX Chicago From Chicago / Milwaukee From Los Angeles Los Angeles Oneworld

United and American Airlines have round-trip flights from Chicago (ORD) to Punta Cana (PUJ) for $275-$288. Flights from August to March. No Weekends. Departures on Monday, Tuesday, Wednesday, and Thursday. Very few extended weekends available. Origin/Destination reversible.

Note: United “Basic Economy” flights are NONSTOP, but 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: American Airlines flights allow for a free carry-on bag, but have a connection.

Read More Nonstop Flights: Chicago to/from Punta Cana $275-$288 r/t – United / American

Airfare Deals American Airlines Bookable Chicago Bookable Deals From Chicago / Milwaukee Oneworld Punta Cana Star Alliance United

Airfare Deals Bookable Chicago Bookable Deals Delta From Chicago / Milwaukee Liberia (Costa Rica) SkyTeam

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

[07/26/2019 @ 03:35 PM CT] Fare seems to have been removed by Star Alliance. If it goes back online, we will send out another notification.

SWISS, Lufthansa, Air Dolomiti, United, and various other airlines have round-trip flights from Chicago (ORD) to Venice (VCE) for $475-$553 with a connection. Flights October to March. No Saturday departures. 7-day minimum stay required. Cheapest flights depart on Tuesdays or Wednesdays.

Note: Lufthansa “Light Fares” allow for 1 carry-on bag with a maximum weight restriction of 18-lbs. This will probably not be enough weight for those of you who wish to do a carry-on only trip. You can avoid seat selection fees by accepting the randomly assigned seat at the gate.

Read More Cheap Flights: Chicago to Venice $475-$553 r/t – SWISS / Lufthansa / Air Dolomiti / United

Airfare Deals Bookable Chicago Bookable Deals From Chicago / Milwaukee Lufthansa Star Alliance Swiss United Venice

Air France Airfare Deals Bookable Chicago Bookable Deals British From Chicago / Milwaukee KLM Luxembourg Oneworld SkyTeam