"Learning to Fly" by Tom Petty (Thanks, Cryton!)

Expecting to fly - Buffalo Springfield

Above the Clouds -- Paul Weller

Come Josephine In My Flying Machine - Spike Jones and His City Slickers

Artists:

Love and Rockets

You’ll Never Get Me Up In One Of Those - Mickey Jupp
Rocket Number 9 - Sun Ra; NRBQ

Bermuda Triangle Blues (Flight 45)--Blondie
Ghost of Flight 401--Bob Welch
Let's Roll--Neil Young
Hits of the Year--Squeeze (about a hijacking)
Coming into Los Angeles--Arlo Guthrie
5 Miles Out--Mike Oldfield (based on a real incident of a plane in trouble)
Drop the Pilot--Joan Armatrading
Shut Up and Die Like an Aviator (album)--Steve Earle

GROUPS
Flying Machine (early James Taylor)
Flying Machine ("Smile a Little Smile For Me", 70s one-hit wonder)

Magic Carpet Ride - Steppenwolf
Gotta Get Back - Shelby Lynne ("I can almost touch you now / flying above the clouds in a big ol' plane...")
Fire and Rain - James Taylor ("...sweet dreams and flying machines in pieces on the ground...")
Paper Aeroplane - KT Tunstall
Paper Wings - Gillian Welch
Superman - Barbra Streisand
Fly Away - John Denver
To Live is to Fly - Cowboy Junkies
Flying Down to Rio - Fred Astaire & Ginger Rogers
Fly Away - Lenny Kravitz
Flying Down Juniper - Lindsey Buckingham

From An Airplane Window - Roman Candle
Flying - Joe Jackson
Fly- David Bowie
Aeroplane - Robert Palmer
Launch Pad - Some Girls
Air Miles - John Taylor
Flying Circles - Ariel Pink

Artists:

Stone Temple Pilots

Icarus - Borne On The Wings of Steel - Kansas
Icarus Ascending - Dan Fogelberg

Crazy in the Night (Barking at Airplanes)--Kim Carnes
Helicopter--Red House Painters
ME 262--Blue Oyster Cult (ME 262 = WW2 German war plane)
You Are My Starship--Norman Connors
I Wish I Could Fly Like Superman--Kinks
This Flight Tonight--Nazareth
U2--Negativland
Apollo 18 (album)--They Might Be Giants
Here Come the Warm Jets (album)--Eno

GROUP: U2

Burning Airlines Give You So Much More -- Brian Eno
Fly Me Away -- Goldfrapp

Come Take A Trip In My Airship-Natalie Merchant

"Rocketship" - The Dead Milkmen
"Helicopter Interiors" - The Dead Milkmen
"Air Crash Museum" - The Dead Milkmen

Barbados - Typically Tropical (starts off with flight captain's announcement)

album:

Jefferson Airplane Takes off - Jefferson Airplane

Love Me Like a Rocket - Kate Garner
Young Pilot Astray - Ariel Pink

Album:

Rocket - Primative Radio Gods

I was trying to remember the name of this song. It's one of those big UK hits that's virtually unkown in the US.

Blues From an Airplane--Jefferson Airplane
Flight 602--Chicago
Apollo 9--Adam Ant
Fireball XL-5--XTC (cover of the TV theme song)

Running Dry (Requiem for the Rockets) -- Neil Young

By the way, The Rockets were a band that later was known as Crazy Horse.