Flights from Chicago (ORD)
Find cheap flights from Chicago (ORD). BookingTrolley tracks fares to 30+ popular destinations and shows which airlines depart Chicago.
Popular domestic destinations from Chicago
- to DetroitDTW · United States · 376 kmView →
- to MinneapolisMSP · United States · 537 kmView →
- to CharlotteCLT · United States · 964 kmView →
- to AtlantaATL · United States · 976 kmView →
- to New YorkEWR · United States · 1,154 kmView →
- to New YorkJFK · United States · 1,188 kmView →
- to DallasDFW · United States · 1,290 kmView →
- to BostonBOS · United States · 1,391 kmView →
- to DenverDEN · United States · 1,426 kmView →
- to HoustonIAH · United States · 1,489 kmView →
- to OrlandoMCO · United States · 1,620 kmView →
- to MiamiMIA · United States · 1,930 kmView →
Popular international destinations from Chicago
- to TorontoYYZ · Canada · 701 kmView →
- to MontrealYUL · Canada · 1,201 kmView →
- to MonterreyMTY · Mexico · 2,119 kmView →
- to CancunCUN · Mexico · 2,330 kmView →
- to Mexico CityMEX · Mexico · 2,718 kmView →
- to GuadalajaraGDL · Mexico · 2,789 kmView →
- to VancouverYVR · Canada · 2,831 kmView →
- to San SalvadorSAL · El Salvador · 3,175 kmView →
- to Panama CityPTY · Panama · 3,753 kmView →
- to BogotaBOG · Colombia · 4,363 kmView →
- to DublinDUB · Ireland · 5,897 kmView →
- to LimaLIM · Peru · 6,105 kmView →
- to ManchesterMAN · United Kingdom · 6,140 kmView →
- to LondonLHR · United Kingdom · 6,345 kmView →
- to AmsterdamAMS · Netherlands · 6,613 kmView →
- to ParisCDG · France · 6,665 kmView →
- to MadridMAD · Spain · 6,744 kmView →
- to FrankfurtFRA · Germany · 6,971 kmView →
About flights from Chicago
From Chicago (ORD), BookingTrolley compares fares across 30+ popular destinations so you can see where flights are cheapest before you book.
Domestic favourites include Detroit, Minneapolis, Charlotte, while popular international routes head to Toronto, Montreal, Monterrey. The shortest hop on this list is Chicago–Detroit at about 376 km, and longer hauls like Chicago–Toronto suit travellers comparing nonstop and one-stop fares.
Airlines operating from Chicago include United Airlines, American Airlines, Delta Air Lines and Southwest Airlines. BookingTrolley compares their published fares alongside other carriers, so you can weigh price against flight time, stops and baggage on every ORD departure.
Frequently asked questions about flights from Chicago
- Where can I fly from Chicago (ORD)?
- From Chicago you can fly to 30+ destinations tracked by BookingTrolley, including domestic routes such as Detroit, Minneapolis, Charlotte and international destinations like Toronto, Montreal, Monterrey. Compare live fares to pick the cheapest destination for your dates.
- Which airlines fly from Chicago?
- Airlines departing Chicago (ORD) include United Airlines, American Airlines, Delta Air Lines and Southwest Airlines, among others. BookingTrolley compares published fares across these carriers so you can see which is cheapest on your chosen route.
- How do I find the cheapest flights from Chicago?
- To find the cheapest flights from Chicago, compare destinations on flexible dates, avoid Friday–Sunday peaks, and book international routes like Chicago to Toronto a few weeks ahead. BookingTrolley shows the lowest live fare for each destination so you can compare at a glance.
- When is the best time to book flights from Chicago?
- Mid-week departures from Chicago are often cheaper than weekends, and booking 3–8 weeks ahead usually secures lower fares on popular routes. BookingTrolley tracks fare movements from ORD so you can book when prices dip.
- Are there direct flights from Chicago?
- Many short-haul routes from Chicago, such as Chicago to Detroit, are served nonstop, while longer international routes like Chicago to Toronto may include a connection depending on the airline. Compare nonstop and one-stop fares on BookingTrolley to find the best balance of price and travel time.