JetBlue has round-trip flights from Chicago (ORD) to Nassau, Bahamas (NAS) for $279-$284 with a connection. Flights August to September. Departures on Monday, Tuesday, Wednesday, Saturday, and Sunday. Origin/Destination reversible.
Category: <span>Flights from Chicago / Milwaukee</span>
Image Credits: Norm Lanier, Creative Commons 2.0 (flickr)
Image Credits: yeowatzup, Creative Commons 2.0
United, Southwest, and American Airlines have round-trip flights from Chicago (ORD/MDW) to Pittsburgh or Fort Lauderdale (PIT, FLL) for $137-$194, NONSTOP. Flights May to October. Departures on Monday, Tuesday, Wednesday, Thursday, and Saturday. Origin/Destination reversible.
Pittsburgh fares range from $137-$158.
Fort Lauderdale fares range from $169-$194.
Image Credits: Kasuga Huang, Creative Commons 3.0
Sometimes flights to Hawaii are cheaper out of Milwaukee…
Southwest and United have round-trip flights from Milwaukee (MKE) to Maui-Kahului, Honolulu, or Kona, Hawaii (OGG, HNL, KOA) for $360-$434 with a connection. Flights August to November. No weekend departures. Origin/Destination reversible. No Thanksgiving dates.
Image Credits: Robert S. Donovan, Creative Commons 2.0
American Airlines, United, and Southwest have round-trip flights from Chicago (ORD/MDW) to Cincinnati (CVG) for $157-$174, NONSTOP. Flights May, June, August, and September. Departures on Monday, Tuesday, Wednesday, Thursday, and Saturday. Origin/Destination reversible.
Image Credits: Captured Visuals, Creative Commons 2.0 (flickr)
United and American Airlines have round-trip flights from Chicago (ORD) to Portland, Maine (PWM) for $173-$192, NONSTOP. Flights May, June, August, and September. Departures on Monday, Tuesday, Wednesday, Thursday, and Saturday. Origin/Destination reversible.
Nonstop Flights: Chicago to/from Montego Bay, Jamaica $318-$328 round-trip [April-March] – Southwest
Image Credits: Public Domain
Nonstop Flights: Chicago to/from Montego Bay, Jamaica $318-$328 round-trip [April-March] – Southwest
Southwest has round-trip flights from Chicago (MDW) to Montego Bay, Jamaica (MBJ) for $318-$328, NONSTOP. Flights April to March. Weekends available. Origin/Destination reversible.
Image Credits: Plashing Vole, Creative Commons 2.0 (flickr)
United, Southwest, and American Airlines have round-trip flights from Chicago (ORD/MDW) to Austin, Charlotte NC, or Phoenix (AUS, CLT, PHX) for $155-$191, NONSTOP. Flights May, June, August, and September. Departures on Monday, Tuesday, Wednesday, Thursday, and Saturday. Origin/Destination reversible.
Image Credits: Thomas Hawk, Creative Commons 2.0 (flickr)
United, Southwest, and American Airlines have round-trip flights from Chicago (ORD/MDW) to New York (LGA) for $129-$152, NONSTOP. Flights May, June, August, and September. Departures on Monday, Tuesday, Wednesday, Thursday, and Saturday. Origin/Destination reversible.
American Airlines has round-trip flights from Chicago (ORD) to Kauai (LIH) for $318 with a connection. Flights August to September. Departures on Monday, Tuesday, and Wednesday. Origin/Destination reversible.
United, Southwest, and American Airlines have round-trip flights from Chicago (ORD/MDW) to Cleveland (CLE) for $97-$144, nonstop. Flights May, June, and August. Departures on Monday, Tuesday, Wednesday, Thursday, and Saturday. Origin/Destination reversible.
Image Credits: Adnan Islam
Delta has round-trip flights from Chicago (MDW/ORD) to Baltimore, Charleston, Houston, Charlotte, Jacksonville, Myrtle Beach, Sarasota, or Raleigh (BWI, CHS, IAH, CLT, JAX, MYR, SRQ, RDU) for $167-$173 with a connection. Flights May to February. Weekends available.
Image Credits: Rambla, Creative Commons 2.0 (wikipedia)
Tap Air Portugal has round-trip flights from Chicago (ORD) to Barcelona (BCN) for $514-$538 with a connection. Flights October to January. Departures on Wednesday. 7-day minimum stay required.
Image Credits: Public Domain
United has round-trip flights from Chicago (ORD) to Montego Bay, Jamaica (MBJ) for $318-$343, NONSTOP. Flights April to January. Very few weekends available. Origin/Destination reversible.
Image Credits: Nrbelex, Creative Commons 2.0
American Airlines has round-trip flights from Chicago (ORD) to Atlanta (ATL) for $131-$147, NONSTOP. Flights April, May, August, September, October, November, December. Departures on Tuesday, Wednesday, and Saturday. Origin/Destination reversible. Holiday blackouts.
November and December dates are limited. Use the example date list to pull up dates that work.
Image Credits: Cristo Vlahos, Creative Commons 3.0
United has round-trip flights from Chicago (ORD) to Honolulu, Hawaii (HNL) for $342-$353, nonstop or with connections. Flights April to May. Departures on Monday, Tuesday, and Wednesday. Origin/Destination reversible.
Image Credits: Thomas Hawk, Creative Commons 2.0 (flickr)
United has round-trip flights from Chicago (ORD) to Minneapolis, New Orleans, Newark/New York, Orlando, Philadelphia, Pittsburgh, San Diego, St. Louis, Tampa, or Washington D.C. for $91-$140, NONSTOP. Flights March to May. Departures on Tuesday, Wednesday, and Saturday.
United, jetBlue, and American have round-trip flights from Chicago (ORD) to Cleveland, Cincinnati, Charlotte NC, Boston, Baltimore, Atlanta, Fort Lauderdale, Houston, Indianapolis, or Los Angeles for $91-$160, NONSTOP. Flights March to May. Departures on Tuesday, Wednesday, and Saturday. Origin/Destination reversible.
Most fares are on United.
Nonstop Flights: Chicago to/from Vail, Colorado $241 round-trip [March] – American Airlines / United
Image Credits: Kevin Bovard, Creative Commons 2.0 (flickr)
Nonstop Flights: Chicago to/from Vail, Colorado $241 round-trip [March] – American Airlines / United
American Airlines and United have round-trip flights from Chicago (ORD) to Vail, Colorado (EGE) for $241, NONSTOP. Flights in March. Departures on Monday, Tuesday, and Sunday. Origin/Destination reversible.
American Airlines has round-trip flights from Chicago (ORD) to Honolulu (HNL) for $341-$356, NONSTOP. Flights March to May. Departures on Monday, Tuesday, Wednesday, and Sunday.
Image Credits: Chris Gin, Creative Commons 2.0 (flickr)
Air Canada has round-trip flights from Chicago (ORD) to Auckland, New Zealand (AKL) for $579 with a connection. Flights February to March.
Earlier today this was $649, it’s now dropped to a new low of $579.
This has a long 5-hour connection on the outbound leg of this flight, but at this price, I think it’s worth the time.