American Airlines has round-trip flights from Chicago (ORD) to Honolulu or Maui, Hawaii (HNL) for $415-$445, NONSTOP. Flights in November, January, and February. Departures on Monday and Tuesday. Origin/Destination reversible. No Thanksgiving dates. Limited calendar availability.
Maui fares have more dates available than Honolulu, but it is limited to January only.
Southwest, American Airlines, and United have round-trip flights from Chicago (MDW/ORD) to Pittsburgh (PIT) for $137-$142, NONSTOP. Flights August to December. Very few weekends available. No Christmas dates available.
Scandinavian Airlines has round-trip flights from Chicago (ORD) to Oslo (OSL) for $409-$427 with a connection. Flights January to March. No Wednesday departures.
Icelandair has round-trip flights from Chicago (ORD) to Stockholm (ARN) for $352-$400 with a connection. Flights September to December. No Christmas dates available.
Turkish Airlines has round-trip flights from Chicago (ORD) to Istanbul (IST) for $750, NONSTOP. Flights September to February.
Frontier has round-trip flights from Chicago (ORD) to Los Angeles or Houston (LAX, IAH) for $68-$100, NONSTOP. Los Angeles flights August to September. Houston flights August to November. No Sunday departures. Very few weekends available. Origin/Destination reversible.
Icelandair has round-trip flights from Chicago (ORD) to Berlin (BER) for $470-$506 with a connection. Flights September to December. No Christmas dates available.
Icelandair has round-trip flights from Chicago (ORD) to Amsterdam (AMS) for $508-$552 with a connection. Flights September to December. No Christmas dates available.
Scandinavian Airlines has round-trip flights from Chicago (ORD) to Helsinki (HEL) for $452-$474 with a connection. Flights October to December. No Saturday departures. No Christmas dates available.
United, American Airlines, Delta, Southwest and various other airlines have round-trip flights from Chicago (ORD/MDW) to New York (LGA/JFK) for $135-$143, NONSTOP. Flights August to December. Departures on Monday, Tuesday, Wednesday, Thursday, and Saturday. Origin/Destination reversible. No Christmas dates available.
Southwest has round-trip flights from Denver (DEN) to Chicago or Seattle (MDW, SEA) for $155-$172, NONSTOP. Flights August to December. Departures on Monday, Tuesday, Wednesday, Thursday, and Saturday. Origin/Destination reversible. No Christmas dates available.
American Airlines and Southwest have round-trip flights from New York (LGA) to Chicago, New Orleans, or Nashville (ORD/MDW, MSY, BNA) for $99-$171, NONSTOP. Flights August to December. Departures on Monday, Tuesday, Wednesday, Thursday, and Saturday. No Christmas dates available.
Nashville ($99) is the cheapest fare in this group.
Southwest and American have round-trip flights from Chicago (MDW/ORD) to New Orleans or Phoenix (MSY, PHX) for $157-$190, NONSTOP. Flights August to December. Departures on Monday, Tuesday, Wednesday, Thursday, and Saturday. Origin/Destination reversible. No Christmas dates available.
JetBlue has round-trip flights from Chicago (ORD) to Nassau, Bahamas (NAS) for $322-$335 with a connection. Flights August to September. No Thursday departures. Origin/Destination reversible.
American Airlines has round-trip flights from Chicago (ORD) to Kingston, Jamaica (KIN) for $397-$403 with a connection. Flights September to October. Weekends available. Origin/Destination reversible.
American Airlines, United, and Southwest have round-trip flights from Chicago (ORD/MDW) to Columbus or Memphis (CMH, MEM) for $157, NONSTOP. Flights July to December. Departures on Tuesday, Wednesday, and Saturday. No Christmas dates available.
Southwest, American Airlines, and United have round-trip flights from Chicago (MDW/ORD) to Pittsburgh (PIT) for $137, NONSTOP. Flights July to December. Departures on Tuesday, Wednesday, and Saturday. No Christmas dates available.
Delta, Virgin Atlantic, and Air France have round-trip flights from Chicago (ORD) to Reykjavik (KEF) for $321-$334 with a connection. Flights August to October.
SkyTeam code-share may fly on other carriers within alliance.
JetBlue has round-trip flights from Chicago (ORD) to Aruba (AUA) for $377-$404 with a connection. Flights in September. Departures on Monday, Tuesday, Wednesday, and Sunday.
United, JetBlue, and Southwest have round-trip flights from Chicago (ORD/MDW) to Fort Lauderdale (FLL) for $167-$171, NONSTOP. Flights July to December. Departures on Tuesday, Wednesday, and Saturday. No Christmas dates available.
