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.
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Minneapolis–St. Paul (MSP) Snow Day Guide: Parking, Lounges, and $2.50 Transit When Your Flight Melts Down
How to use Minneapolis–Saint Paul International Airport’s parking, terminals, lounges, and transit to turn winter delays into a functional workday instead of a white‑knuckle slog.
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 airport parking and light rail: how MSP’s ground game saves (or burns) your money
Minneapolis–Saint Paul International Airport (MSP) looks simple on the map, but 12 parking products, a $2–$2.50 light rail, and 12 lounges mean your ground choices can swing trip cost by hundreds a year. Here is the data
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.