O'Hare's advantage is international, not domestic
Chicago is one of the few American cities where a family genuinely chooses its airport, and the choice usually gets made on a hunch: O'Hare is the big one, Midway is the small one, so O'Hare must have more of everything. The Chicago Department of Aviation publishes the actual counts, and they say something more useful than "bigger".
| As of August 2026 | O'Hare (ORD) | Midway (MDW) |
|---|---|---|
| US cities served nonstop | 197 | 83 |
| International destinations nonstop | 69 | 9 |
| Daily nonstop departures, domestic | About 1,161 | About 223 |
| Carriers you will mostly meet | United and American | Southwest |
Sort by nonstops per day, not flight time
Every nonstop roundup ranks destinations by flight time, including our own from LAX and SFO. Flight time is the wrong sort key once children are involved, because the thing that wrecks a family trip is rarely three hours in a seat. It is a cancelled flight, a rebooking queue, and one middle seat left on Thursday.
What protects you is frequency: how many more nonstops leave that day on the same route. Southwest publishes that figure route by route, drawn from Department of Transportation scheduled data, and it varies far more than flight time does. These are its published weekday counts from Midway.
| From Midway | Flight time | Nonstops per weekday |
|---|---|---|
| Nashville (BNA) | 1h 25m | 5 |
| New Orleans (MSY) | 2h 14m | 3 |
| Tampa (TPA) | 2h 30m | 3 |
| Orlando (MCO) | 2h 31m | 6 |
| Denver (DEN) | 2h 38m | 6 |
| Cancun (CUN) | 3h 36m | 1 |
| Phoenix (PHX) | 3h 45m | 8 |
| San Diego (SAN) | 4h 19m | 3 |
Two or three nights: the weekend map
A long weekend only survives a flight of about two and a half hours or less, because anything longer spends the whole of Friday and most of Sunday in transit. Three destinations clear that bar from Chicago with real frequency behind them.
- Nashville is the shortest of the three at 1h 25m from Midway, close enough that a delayed flight still leaves you with a Friday evening.
- New Orleans at 2h 14m is the one that feels furthest from Illinois for the least flying.
- Denver at 2h 38m is marginal for two nights and comfortable for three, with six weekday nonstops from Midway plus American, Frontier and United from O'Hare.
A school-break week: where O'Hare starts to matter
Give the trip a full week and a drive-free beach week becomes realistic, and this is the first bucket where the airports genuinely diverge. Two of these run from both airports, and the difference between them is the whole argument of this page.
- Both airports: Orlando, six weekday nonstops on Southwest from Midway, plus American, Frontier and United from O'Hare. If a theme-park week is the plan, our Disney World versus Universal breakdown is the decision before the flight.
- Both, but thinly: Myrtle Beach flies from O'Hare on American and United, and from Midway on Southwest at one nonstop per weekday. Same sand, very different options if that flight goes.
- O'Hare only: Destin-Fort Walton Beach (VPS, American) and Fort Myers (RSW, American and United) on the Gulf. Neither carries a Southwest nonstop published from Midway.
The Gulf pair is the real argument for O'Hare on a domestic trip: a beach week with no connection for a child to sit through. A connection through Atlanta with a five-year-old costs more than the fare difference usually saves.
A winter-sun escape: O'Hare wins outright
February is when the airport question answers itself. Midway's nine international destinations are thin on the Caribbean; O'Hare's sixty-nine are not. Every route below is a published O'Hare nonstop as of August 2026.
| Winter-sun nonstop | Code | Carriers |
|---|---|---|
| Aruba | AUA | United |
| Turks and Caicos | PLS | United |
| Grand Cayman | GCM | United |
| Punta Cana | PUJ | American, United, Arajet |
| Nassau | NAS | American, United |
| Montego Bay, Jamaica | MBJ | American, United |
| San Jose, Costa Rica | SJO | United |
| Cancun | CUN | American, Frontier, United |
Cancun is the one destination on this page that both airports serve, which makes it the cleanest illustration of the trade. Midway gives you Southwest and one flight a day. O'Hare gives you three carriers and the ability to be rebooked the same afternoon.
How far is too far, by kid age
The practical version for Chicago: the sub-three-hour list is a normal flight for almost any age, and the four-plus-hour routes such as San Diego are the ones worth matching against your own child rather than a rule. Frequency helps here too, because a flight you can move is a flight you can move to a better time of day.
Before you book
- Check the route still exists. Nonstop maps move seasonally, and both airport lists above are August 2026 snapshots. Verify on the airline's own site before you pay.
- Count the nonstops on your date. The weekday figures are scheduled averages; a Tuesday in February is not a Friday in July.
- Price the ground trip too. Midway is closer to the Loop and materially smaller to walk with a stroller; O'Hare buys reach and costs you terminal.
- Pick the season before the destination. Our guide to the best time of year to travel with kids narrows the map faster than any flight search.
If you are still deciding between the beach week and the city break, start from the destination end instead: our Chicago family guide covers the home side, and airport security with kids is the part of the day both airports share.