Flights
Flights to Chicago
Flying to Chicago for a game, a concert or a show? The airport you pick decides the rest of the trip more than the fare usually does. This page lists the 2 airports with scheduled flights near Chicago, how far each is from the centre and which is nearest each of the city's main venues. StubOrder lists 4,546 upcoming events in and around Chicago (counted Sep 24, 2026); fares are searched live when you pick your dates.
The closest airport to downtown Chicago is Chicago Midway International Airport (MDW), 9 miles away. Chicago O'Hare International Airport (ORD) is 16 miles away. For Mainstage at Second City - Chicago, the nearest is MDW at 11 miles. Search CHI to compare every Chicago airport at once.
Airports serving Chicago
Nearest first. Distances are straight-line from the centre of Chicago, which is the fair way to compare airports with each other; the drive is always longer.
| Airport and distance from the centre | Type | Notes |
|---|---|---|
| Chicago Midway International Airport (MDW) 9 mi (15 km) | Large | About 12 miles south-west of the Loop, boxed into a residential street grid, and far smaller and quicker to move through. It is Southwest Airlines' Chicago base, so if you are flying Southwest you are almost certainly flying here. The CTA Orange Line terminates at the airport and reaches the Loop in around 20 to 25 minutes, which makes Midway the faster arrival to downtown despite being the less famous option. Unlike the Blue Line, though, the Orange Line is not a 24-hour service: it closes for a few hours overnight, so check the last train before you rely on it for a very late landing. |
| Chicago O'Hare International Airport (ORD) 16 mi (26 km) | Large | About 18 miles north-west of the Loop, and by a wide margin the larger of the two. It is a hub for both American and United and carries essentially all of Chicago's international service. The CTA Blue Line leaves from a station beneath the terminals and reaches downtown in roughly 45 minutes, and it runs 24 hours a day — the single most useful fact about arriving in Chicago, because a delayed late flight never strands you. Driving in is 30 to 45 minutes in theory and often much worse; the Kennedy Expressway is one of the more reliably congested roads in the country. Note that the CTA charges a higher fare for boarding the L at O'Hare specifically; the return journey is the ordinary flat fare. |
Which airport for which venue
The busiest venues in and around Chicago, each with its own nearest airport. A stadium in the suburbs is often nearer a different airport than downtown is, so this is the table to book from.
| Venue | Nearest airport we list | Second option |
|---|---|---|
| Mainstage at Second City - Chicago Hotels near Mainstage at Second City - Chicago | MDW, 11 mi | ORD, 15 mi |
| Orchestra Hall At Chicago Symphony Center Hotels near Orchestra Hall At Chicago Symphony Center | MDW, 9.2 mi | ORD, 16 mi |
| Zanies Comedy Club - Chicago Hotels near Zanies Comedy Club - Chicago | MDW, 11 mi | ORD, 15 mi |
| United Center Hotels near United Center Airports near United Center | MDW, 7.7 mi | ORD, 14 mi |
| Metropolis Performing Arts Centre Hotels near Metropolis Performing Arts Centre | ORD, 8.3 mi | MDW, 24 mi |
| Lyric Opera House - IL Hotels near Lyric Opera House - IL | MDW, 8.9 mi | ORD, 15 mi |
| Zanies Comedy Club - Rosemont Hotels near Zanies Comedy Club - Rosemont Airports near Zanies Comedy Club - Rosemont | ORD, 1.9 mi | MDW, 15 mi |
| Cadillac Palace Hotels near Cadillac Palace | MDW, 9.1 mi | ORD, 15 mi |
- Metropolis Performing Arts Centre is nearer ORD (8.3 mi) than MDW (24 mi).
- Zanies Comedy Club - Rosemont is nearer ORD (1.9 mi) than MDW (15 mi).
Which airport is nearest the venues
Each upcoming event in and around Chicago counted against the first airport we list for its venue, as of Sep 24, 2026. More than one airport is first for a real share of them, so the right one depends on where you are going.
| Airport | Share of events | Of the busiest venues |
|---|---|---|
| MDW | 6 of 8, including Mainstage at Second City - Chicago | |
| ORD | 2 of 8, including Metropolis Performing Arts Centre |
Venue by airport
Straight-line miles from each of the busiest venues to each airport; the nearest is in bold.
| Venue | MDW | ORD |
|---|---|---|
| Mainstage at Second City - Chicago | 11 mi | 15 mi |
| Orchestra Hall At Chicago Symphony Center | 9.2 mi | 16 mi |
| Zanies Comedy Club - Chicago | 11 mi | 15 mi |
| United Center | 7.7 mi | 14 mi |
| Metropolis Performing Arts Centre | 24 mi | 8.3 mi |
| Lyric Opera House - IL | 8.9 mi | 15 mi |
| Zanies Comedy Club - Rosemont | 15 mi | 1.9 mi |
| Cadillac Palace | 9.1 mi | 15 mi |
Home teams and their airports
| Team | Home venue | First airport | League |
|---|---|---|---|
| Chicago Bears | Soldier Field | MDW, 8.7 mi | NFL stadium airports |
| Chicago Cubs | Wrigley Field | MDW, 12 mi | MLB ballpark airports |
| Chicago White Sox | Rate Field | MDW, 6.8 mi | MLB ballpark airports |
| Chicago Bulls | United Center | MDW, 7.7 mi | NBA arena airports |
| Chicago Blackhawks | United Center | MDW, 7.7 mi | NHL arena airports |
| Chicago Fire FC | Soldier Field | MDW, 8.7 mi | MLS stadium airports |
| Chicago Sky | Wintrust Arena | MDW, 8.2 mi | WNBA arena airports |
Flying in for a Chicago event
In the next 30 days (counted Sep 24, 2026): 1,231 events in and around Chicago; 65% on Fri–Sun; 886 of the 1,169 with a set time start at 7 pm or later, local time.
Fly in the day before an evening event: a delayed afternoon flight is a missed show. Plan to fly home the morning after, because the last departures of the night often leave before a late finish lets out. The dates below set the search to do exactly that, around each event.
Chicago Architecture Foundation - River Cruise (Multiple Dates and Times)
Chicago Architecture Center, Chicago, Illinois
Cold Waves XIV Chicago - 3 Day Pass
Metro Chicago, Chicago, Illinois
Chicago Symphony Orchestra: Klaus Makela - Sibelius & Shostakovich
Orchestra Hall At Chicago Symphony Center, Chicago, Illinois
From about $79.00View TicketsLucy Darling
Studebaker Theater, Chicago, Illinois
From about $116.00View TicketsBeyond The Gate: Cate Le Bon & Horsegirl
Bohemian National Cemetery, Chicago, Illinois
From about $88.00View TicketsThe Second City Mainstage 114th Revue
Mainstage at Second City - Chicago, Chicago, Illinois
Candlelight: Tribute to The Beatles
The Arts Center of Oak Park, Oak Park, Illinois
From about $76.00View TicketsChicago White Sox vs. Colorado Rockies
Rate Field, Chicago, Illinois
From about $28.00View Tickets
Search flights for:
- Sep 25: Chicago Architecture Foundation - River Cruise …
- Sep 25: Beyond The Gate: Cate Le Bon & Horsegirl
Flying in to Chicago: checklist
- Book the airport for your venue. For Mainstage at Second City - Chicago it is MDW, 11 miles away; the table above has the rest.
- Compare the airports at once. Search CHI instead of one airport to see fares into the Chicago airports it covers side by side.
- Arrive the day before an evening event, and plan the flight home for the next morning.
- Names exactly as on the ID. The airline compares the booking with the ID at the airport.
- Check the bag allowance. It is shown on every fare; extra bags are not part of the fare price.
Plan the rest of the trip
Frequently asked questions
Can I buy event tickets and flights together?
Not as one purchase. Event tickets come from our resale marketplace and flights from our travel partner and the airlines, as separate bookings with separate confirmations. Neither depends on the other, so if an event moves, your flight does not change automatically.
Which Chicago venues are closer to ORD?
Of the busiest Chicago venues, Metropolis Performing Arts Centre (8.3 mi, against 24 mi to MDW) and Zanies Comedy Club - Rosemont (1.9 mi, against 15 mi to MDW) are nearer ORD than MDW in a straight line. Fares differ by date, so compare both when you search.
How far is MDW from downtown Chicago?
Chicago Midway International Airport (MDW) is 9 miles (15 km) from downtown Chicago in a straight line. The drive is always longer than the straight line, and the roads near the venues are busiest at event times, so allow more than a map suggests.
What is the closest airport to Chicago?
Chicago Midway International Airport (MDW) is the closest airport with scheduled flights to downtown Chicago, 9 miles away in a straight line. StubOrder also lists ORD (16 miles).
Which airport is closest to the Chicago Bears' home stadium?
The Chicago Bears and the Chicago Fire FC play home games at Soldier Field. The closest airport to Soldier Field is Chicago Midway International Airport (MDW), 8.7 miles away in a straight line.
Which airport is closest to the Chicago Cubs' home ballpark?
The Chicago Cubs play home games at Wrigley Field. The closest airport to Wrigley Field is Chicago Midway International Airport (MDW), 12 miles away in a straight line.
Which airport is nearest most Chicago venues?
Chicago Midway International Airport (MDW) is the first airport we list for the venues holding 73% of upcoming events in and around Chicago (as of Sep 24, 2026); ORD for 27%. Distances are straight lines from each venue.
Which airport is best for Orchestra Hall At Chicago Symphony Center?
The closest airport to Orchestra Hall At Chicago Symphony Center is Chicago Midway International Airport (MDW), 9.2 miles away in a straight line; Chicago O'Hare International Airport (ORD) is 16 miles. Fares differ by date, so compare both when you search.
Are fares shown on this page?
No. Airline fares change by the minute and depend on your exact dates, airports and travellers, so this page shows none. Pick your dates in the search form and StubOrder asks the airlines live; every fare it shows is the total for all travellers, taxes and fees included.
How many events are in Chicago in the next 30 days?
1,231 in and around Chicago in the 30 days from Sep 24, 2026, when this page's figures were counted. 65% of them fall on a Friday, Saturday or Sunday, and 886 of the 1,169 with a set start time begin at 7 pm or later, local time.
Which airport is best for Mainstage at Second City - Chicago?
The closest airport to Mainstage at Second City - Chicago is Chicago Midway International Airport (MDW), 11 miles away in a straight line; Chicago O'Hare International Airport (ORD) is 15 miles. Fares differ by date, so compare both when you search.
How many airports serve Chicago?
StubOrder lists 2 airports with scheduled passenger flights within 100 km (62 miles) of downtown Chicago: Chicago Midway International Airport (MDW) and Chicago O'Hare International Airport (ORD). Airlines also sell CHI as one code covering several Chicago airports, and the search form accepts it.
