ORD + 1 more airports
Cheap Flights to Chicago
Bag fees in the price · compare LAX vs SNA
Things to do in Chicago
See all
2 hours · Free cancellation
Small-Group Sightseeing Boat Tour in Chicago
5.0★ · 121 reviews
From $89
2 hours · Free cancellation
Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago
5.0★ · 73 reviews
From $508
2 hours · Free cancellation
Chicago Walking Tour: Connecting Past and Present
5.0★ · 44 reviews
From $35
Chicago is the third-largest city in the US, home to world-class architecture, deep-dish pizza, Lake Michigan, and some of the finest museums in the country. ORD and MDW serve different airlines and neighborhoods — choosing the right airport can save a family of four $100+ in ground transport.
Search flights to Chicago
Compare flights to ORD across providers. True trip cost with bag fees included.
Airport guide
O'Hare (ORD) is a United and American hub with broad international connections; the Blue Line L train gets you downtown in ~45 minutes for $2.50. Midway (MDW) is Southwest's hub — often cheaper fares, closer to the south side — and the Orange Line connects in ~30 minutes. For Magnificent Mile stays, ORD is typically more convenient.
Family travel tip
Southwest's free bag policy at MDW can turn an apparently pricier MDW fare into the better family deal once you add two checked bags from a legacy carrier at ORD. Spotvoy calculates this automatically.
Best time to visit
May–June and September–October for mild weather. Chicago winters are brutal — January fares are cheap for a reason.
LAX vs SNA to Chicago
Searching "LA to Chicago" usually means LAX, but Orange County (SNA) is often the better true-cost option if you start south of Los Angeles. Compare both with bags included.
Popular routes to Chicago
Common questions about Chicago flights
What airport serves Chicago?
Chicago is served by multiple airports: ORD, MDW. O'Hare (ORD) is a United and American hub with broad international connections; the Blue Line L train gets you downtown in ~45 minutes for $2.50. Midway (MDW) is Southwest's hub — often cheaper fares, closer to the south side — and the Orange Line connects in ~30 minutes. For Magnificent Mile stays, ORD is typically more convenient.
When is the best time to fly to Chicago?
May–June and September–October for mild weather. Chicago winters are brutal — January fares are cheap for a reason.
Is Chicago a good destination for families?
Southwest's free bag policy at MDW can turn an apparently pricier MDW fare into the better family deal once you add two checked bags from a legacy carrier at ORD. Spotvoy calculates this automatically.
How do I find cheap flights to Chicago?
Search Chicago on Spotvoy to compare headline fares plus bag fees and seat costs. Midweek dates and a nearby origin airport often change which option is actually cheapest.
How does Spotvoy find the cheapest flights to Chicago?
We search across multiple flight providers, add bag fees and typical seat costs, and recommend the flight we'd actually book — not just the lowest headline fare.
Are there flights from LA to Chicago?
Yes. Los Angeles (LAX) has regular service to ORD. Compare that fare with Orange County (SNA) if you live south of LA — the easier airport sometimes wins once you add the drive and bag fees.
Should I fly LAX or SNA to Chicago?
It depends on where you start and whether you check bags. SNA is usually faster for south OC and Anaheim; LAX has more frequencies and late flights. Spotvoy prices both with bags included so the headline fare is not the only number.
Things to do in Chicago
Browse tours, day trips, and family activities with live Viator inventory — pair with your flight search for a full trip plan.
Open the Chicago activity shop →