Washington Chicago
Reagan to Midway is the closest thing to downtown-to-downtown flying in the US. Reagan sits four miles from the National Mall, Midway ten miles from the Loop. Southwest runs this pair about a dozen times a day, flight time around two hours.
Reagan to O'Hare is the highest-frequency pair. American, United, and Southwest combine for more than 40 daily departures. If you want a full-service carrier from the closest DC airport and need O'Hare on the Chicago end, this is the easiest route to book last-minute. Codeshare tickets through Alaska, Emirates, and British Airways show up here too.
Dulles to O'Hare is the United hub play. United runs narrowbodies and A321neos all day, and Sun Country flies it if you are watching fares. The trade-off: Dulles is 45 minutes from downtown DC, and the Blue Line from O'Hare into the Loop takes another 45. That is 90 minutes of ground time before you reach anything useful.
BWI covers travelers between DC and Baltimore. Frontier, United, and American all fly to O'Hare, and Southwest flies to Midway. Parking at BWI runs cheaper than Reagan or Dulles.
The split on the Chicago side: Midway to the Loop is 25 minutes on the L for a few dollars. O'Hare to the Loop is closer to 45 minutes. If you are staying downtown, those 20 extra minutes each way add up fast.
Have a specific need? Use the decision guide below to filter by your airline, where you live, lounges, or where you're staying in Chicago.
Pick What Matters to You
Best pair by where you're coming from
Best pair by where you're staying in Chicago
Which pair your airline flies nonstop
| Airline | DCA–ORD | BWI–ORD | IAD–ORD | DCA–MDW |
|---|---|---|---|---|
| American Airlines | ✓ | ✓ | ✓ | — |
| Sun Country Airlines | — | — | ✓ | — |
| Southwest Airlines | ✓ | — | — | ✓ |
| Delta Air Lines | ✓ | — | — | — |
| Frontier | — | ✓ | — | — |
| SkyWest Airlines | — | — | ✓ | — |
| Volaris | — | — | ✓ | — |
| GXA | — | ✓ | — | — |
| United Airlines | ✓ | ✓ | ✓ | — |
| FlyNordic | — | — | — | ✓ |
| TWY | — | — | — | — |
| GoJet Airlines | — | — | ✓ | — |
Ranked by on-time performance
Lounge access by airport and terminal
Ranked by flights per week
Getting to the airport
Red-eye vs daytime departures
Premium cabin options
Connecting through Washington from a domestic flight
All three DC-area airports have nonstop flights to Chicago throughout the day. A connection through a third city adds hours to what is already a two-hour flight. The only scenario where connecting makes sense is if you are starting from a smaller city and routing through Washington or Chicago on the way.
Washington & Chicago Airport Profiles
Each airport has a personality. Terminal quality, transit access, lounge scene, and crowd levels vary dramatically — sometimes more than the flight itself.
Washington Metro
Reagan National sits on the Potomac River, five miles from the National Mall, with monument views on approach. The airport is compact. Terminals B and C handle most traffic, and the walk from security to any gate rarely takes more than ten minutes.
A Metro station connects directly to the terminals on the Blue and Yellow lines. The feel is of a well-run regional airport: shorter concourses, quicker security, and less distance to cover than the area's larger airports. Terminal C has been modernized with better food and more natural light.
BWI sits between Baltimore and Washington, 32 miles from downtown DC and about 10 miles from downtown Baltimore. The airport has a single terminal building divided into concourses A through E, with a straightforward layout that keeps walking distances short.
The terminal is functional rather than flashy. Security checkpoints tend to move faster than at the larger DC-area airports, and the concourses rarely feel overcrowded. A free shuttle bus connects the terminal to the BWI rail station for MARC and Amtrak service.
Dulles sits 27 miles west of downtown Washington in the Virginia suburbs, connected to the city by the Silver Line Metro. The Saarinen-designed main terminal is the building on every postcard, but most gates are in the midfield concourses reached by the AeroTrain people mover.
Walking distances between concourses can be long. If you have a tight connection, check which concourse your gate is in before landing. Security lines can build during the late afternoon departure rush, but TSA PreCheck and Clear lanes move faster.
Chicago Metro
O'Hare has four terminals: Terminal 1, Terminal 2, Terminal 3, and the international Terminal 5. There is no Terminal 4. The terminals spread across a wide footprint connected by the ATS train and underground walkways. Allow 15 to 20 minutes to move between them.
Terminal 5 sits apart from the domestic terminals and handles most international flights. The ATS train connects it to the rest of the airport. Afternoon peaks bring longer security and immigration lines. The terminal is functional and recently updated, but smaller than the domestic concourses.
Terminals 1, 2, and 3 form the domestic core, with more dining and lounge options. The Blue Line train to downtown stops under Terminal 2, accessible from any terminal via the ATS.
Midway is a single-terminal airport on Chicago's southwest side, compact enough to walk end to end in around 10 minutes. One central security checkpoint feeds all concourses. Lines move faster than at larger airports, though holiday weekends and spring break mornings back up. The terminal is older but functional, with food and shops on both sides of security.
Gates are close together and boarding areas are small. Delays mean crowded gate areas with limited seating. The airport handles a high volume of traffic relative to its size. Expect an efficient, basic terminal where everything is a short walk.
Rockford is a small regional airport about 63 miles northwest of downtown Chicago. One terminal with a handful of gates. Security lines are short, and the walk from the parking lot to any gate takes a few minutes. The terminal is quiet outside of departure times, with limited food options.
Parking is close to the building and inexpensive. The trade-off is the drive from the Chicago metro area, which runs 60 to 90 minutes on I-90 depending on traffic and weather.
No high-frequency connections found. Check RFD routes for all options.
Which Airlines Fly Which Pairs
American Airlines and United Airlines serve both DCA and BWI to ORD — airport flexibility on the Washington side.
Not all planes are the same size. The aircraft type below each checkmark tells you whether you are getting a widebody (777, 787, A350) with wider seats and a quieter ride, or a narrowbody (737, A321) with a single aisle. On flights over five hours, the difference is significant.
A319, A320
E170, E175
737-800
A20N
CR2
A319, A320
A319, A320
A321neo, 737-900
737, 737-800
E175
737-800