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.
Category: <span>Flights from Chicago / Milwaukee</span>
Image Credits: Plashing Vole, Creative Commons 2.0 (flickr)
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.
Image Credits: Chris Gin, Creative Commons 2.0 (flickr)
Air Canada has round-trip flights from Chicago (ORD) to Auckland (AKL) for $579-$649 with a connection. Flights February to March.
The outbound segment of this fare has a long connection in Canada; 5-hours, but I think at this price, it may be worth it.
Image Credits: peasap, Creative Commons 2.0
United and American have round-trip flights from Chicago (ORD) to San Diego, Pittsburgh, or Tampa (SAN, PIT, TPA) for $95-$130, NONSTOP. Origin/Destination reversible. No Christmas dates available. Cheapest departures on Tuesday, Wednesday, and Saturday.
San Diego and Pittsburgh: Flights March to December.
Tampa: Flights April, May, July, August, September, October, November, and December.
Image Credits: Nrbelex, Creative Commons 2.0
American Airlines and United have round-trip flights from Chicago (ORD) to Atlanta, Fort Lauderdale, Philadelphia, Cincinnati, Dallas, Houston, or Nashville (ATL, FLL, PHL, CVG, DFW, IAH, BNA) for $91-$164, NONSTOP. Most flights are between February to December, but can vary depending on destination (see example date section on our website.. Cheapest departures on Tuesday, Wednesday, and Saturday. Origin/Destination reversible. No Christmas dates available.
Image Credits: Bernt Rostad, Creative Commons 2.0
American Airlines has round-trip flights from Chicago (ORD) to Las Vegas, San Francisco, Denver, Portland Oregon, or Des Moines (LAS, SFO, DEN, PDX, DSM) for $91-$125, NONSTOP. Flights March to December. Weekends available. Origin/Destination reversible. No Christmas dates available.
Image Credits: Pedro Szekely, creative commons 2.0 (flickr)
Icelandair has round-trip flights from Chicago (ORD) to Stockholm (ARN) for $354-$395 with a connection. Flights in April.
Some small OTAs on Skyscanner have this for as low as $354; which is cheaper than the airline.
Image Credits: Lima Pix, Creative Commons 2.0
Frontier has round-trip flights from Chicago (ORD) to Fort Lauderdale (FLL) for $56-$72, NONSTOP. Flights March to May. Origin/Destination reversible.