Caleb Brockway
Aviation journalist who covered United and American for Crain's Chicago Business 2014-2021. Now writes part-time, mostly about hub politics and carrier strategy.
Caleb covered carrier operations for Crain’s Chicago Business from 2014 until 2021, when the paper restructured and he left to freelance. His beat was the hub politics around O’Hare, the long simmering operational rivalry between United and American, and the regional carrier shuffling that most readers don’t see.
He writes for airport.flights as a paid freelance contributor, one to two pieces a month, focused on Midwest hub operations and the strategy questions behind why a carrier flies what it flies. His beat is the gap between the corporate press release and what’s actually being decided in the operations room. He’s selective about his criticism because he wants to keep being able to call old sources.
He lives in Wicker Park, flies ORD constantly, and tells anyone who’ll listen that the new concourse extensions at ORD are smarter than the consensus admits.
Specialises in
28 notes
St. Louis Lambert vs ORD and DEN: 2 terminals, 82 gates, $2 rail, and when STL wins as a Midwest connection
St. Louis Lambert International Airport’s compact 2-terminal, 82-gate layout, $2–3 rail, four lounges and 12 on-airport parking options make it a smarter, quieter play than routing everything through fortress hubs like O
Kansas City International on Storm Days: The $1.50 Bus vs $50 Rideshare, 7 Parking Options, and 5 Lounges That Actually
Kansas City International Airport (MCI) on thunderstorm days: how 7 parking options, 5 lounges, and the $1.50 RideKC bus change when a 5 p.m. ground stop blows up your plan.
St. Louis Lambert for Same-Day Trips: $7 Parking, $2 Transit, and Why STL Beats a Chicago Drive
How to use St. Louis Lambert’s 12 parking options, $2–3 MetroLink and bus, 4 lounges, and 2-terminal layout to make STL your base for same-day and short trips instead of driving to a mega-hub.
St. Louis Lambert Parking: 12 Lots, $7 Super Park, and When STL Beats ORD and MCI on Weekend Trips
How to use St. Louis Lambert’s 12-lot parking grid and $2 transit like a modular system, and why its $7 Super Park and 2-minute garage walk quietly undercut O’Hare and Kansas City on short trips.
Chicago O’Hare by Ecosystem: United vs American vs Terminal 5 for Parking, Lounges, and the Cheap vs Costly Ride into Ch
ORD parking runs from $0 to $64 a day, O’Hare lounges split into three ecosystems, and the ride to Chicago ranges from $2.25 to $60+. Build your plan by ecosystem first (United, American, Terminal 5), then pick parking,
Does American Airlines Pay for Delays? What You're Owed
American Airlines doesn't pay cash for delays, but you may be owed a refund, meal voucher, or hotel. Here's when — and exactly how to ask.
What Terminal Is Southwest at ORD? Terminal 5 (For Now)
Southwest flies from ORD Terminal 5, gates M2 and M5 — but only until June 3, 2026. The exit timeline, rebooking options, and why Midway wins now.
Chicago O’Hare for Regulars: Ground Transport First, Lounges and Terminals Second
Use Chicago O’Hare like a local commuter hub: CTA Blue Line, Pace buses, Metra, rideshare, plus ORD’s 12 catalogued lounges and 4 terminals. Concrete decision trees for ORD↔Loop, suburb‑to‑suburb via the airport, and wee
What Terminal Is Southwest at STL? Terminal 2, Gates, and the 2031 Move Ahead
Southwest flies from STL's Terminal 2, Concourse E (gates E4-E40). Here's the gate map, the 2025-2026 route cuts, and why Southwest stays put until 2031.
DTW Parking Prices and $2 SMART Bus: How to Use Detroit Metro as a Winter Storm Hedge
Detroit Metro Airport’s 12 catalogued parking options, 12 lounges, and $2 SMART bus make DTW a practical winter storm hedge, if you match the right parking lot to the right escape plan when things break.
DTW Tight Connections: when Detroit’s ‘easy hub’ breaks, and what to do next
Detroit Metro sells an easy-connection story. The real question is what you do once a DTW layover is tight or blown: keep the itinerary, push for a change, ride out a delay in one of 12 lounges, or bail into Detroit on a
MSP parking and transit math: why Terminal 2 quietly wins on $20/day parking and $2 light rail
How to use Minneapolis–St. Paul International Airport’s $20.00/day parking, $2.00–$2.50 METRO Blue Line, and asymmetric lounges to make MSP’s two terminals work for you, not against you.
What Terminal Is American Airlines at ORD? T3 Gate Guide
American's ORD hub is Terminal 3 (Concourses G/H/K/L); Terminal 5 handles int'l arrivals. Real gates, check-in hours, lounges, and how the ATS works.
Chicago O’Hare Delays: How to Use ORD’s 12 Lounges and $2.25 Suburban Buses Instead of Suffering at the Gate
Stuck in a Chicago O’Hare delay? Treat ORD as a regional escape hub, using its 12 lounges and $2.25–$5 transit web to get to the suburbs, Madison, downstate, or downtown instead of stewing in the terminal.
Minneapolis–St. Paul International’s two terminals, 12 lounges, and your missed‑connection risk
Minneapolis–St. Paul International Airport looks simple, but its two-terminal layout hides real differences in lounges, rebooking options, and ground access. Here is how MSP’s terminals, lounges, and transit interact if
St. Louis Lambert parking vs MetroLink: where $7 lots actually beat the $2 train
At St. Louis Lambert International Airport, on-airport parking starts at $7 per day while MetroLink and MetroBus run $2–$3 per ride. Here is when St. Louis airport parking makes more sense than transit if you live on the
Chicago Midway lounges and USO: how a 43‑gate airport became quietly lounge‑dense
Chicago Midway International Airport runs a single commercial lounge plus multiple USO spaces off one 43‑gate terminal. Here is how that actually stacks up for Southwest flyers, what the USO footprint really offers, and
Minneapolis–St. Paul airport lounges: which MSP lounges your card, ticket, or military ID really unlocks
MSP has 12 lounges, but access breaks cleanly by credential: Amex and Priority Pass, airline memberships, and military eligibility. Here is how each group actually plays MSP’s two terminals.
Denver airport lounges for layovers: how to use DEN’s 12 options without missing your flight
Denver International Airport has 12 catalogued lounges split between Jeppesen Terminal and the concourses. Here is how to pick the right Denver airport lounge for your layover or tight connection without losing a bet to
What Terminal Is United at ORD? Terminal 1, 2 & 5 Guide
United's ORD hub is Terminal 1 (Concourses B & C), with United Express in Terminal 2 and int'l arrivals at Terminal 5. Gates, walk times, lounges.
Cleveland, Indianapolis, or Milwaukee: which Midwest ‘little hub’ actually feels big once you’re airside?
For Midwest flyers choosing between Cleveland, Indianapolis, and Milwaukee, the real lounge and food winner changes based on time, budget, and status. Here’s how CLE, IND, and MKE quietly punch above their weight once yo
How I Turn a Chicago Midway Delay into a 20-Minute Food Crawl
Use Chicago Midway International Airport’s single-terminal layout, Central Market cluster, and modest lounge network to turn a delay into a fast, targeted food crawl instead of camping at your gate.
Philadelphia International parking and lounges: the 3 real terminal clusters that decide your trip
Philadelphia International Airport looks like seven neat terminals on paper, but five parking options, real price gaps, and a lopsided 12‑lounge map create three very different ecosystems. Pick the right PHL cluster firs
Denver’s ‘one terminal’ airport is really three: how A, B, and C change your day at DEN
Denver International’s Jeppesen Terminal feels like three airports in Concourses A, B, and C, changing security, connections, lounges, and food
Beating peak‑season prices at Chicago O’Hare International Airport parking without ditching convenience
Flying from Chicago O’Hare International Airport in a busy week? Compare on-site and off-airport parking rates and timing tricks to save.
What you’ll really pay to park at Indianapolis International Airport, from economy to valet
See how parking costs stack up at Indianapolis International Airport, from the cheapest long-term options to close-in premium choices.
How Detroit Metropolitan Wayne County Airport (DTW) Terminals Really Fit Together
Understand Detroit Metropolitan Wayne County Airport terminals, tram, and transfer times beyond the official DTW map.
Leaving your car in St. Louis Lambert International Airport’s Lot A without overpaying
Sorting out St. Louis Lambert International Airport parking—from Lot A to off‑site shuttles—so you don’t spend more than your trip demands.