Route 66 Centennial
TRENDING

Route 66 Centennial

Chicago to Los Angeles, USA · All 2026

2,400Total Miles
8States
100 YearsAnniversary
48+Flight Deals

2026 marks the 100th anniversary of America's most iconic highway. Drive all or part of the 2,400-mile Mother Road from Chicago to Santa Monica — through small towns, desert landscapes, and classic Americana.

Cheap Flights to Route 66 Centennial

American · 2h 30m · Direct
New York
Chicago
Flexible 2026
$210
$89
per person
Book Now
United · 3h 10m · Direct
Miami
Chicago
Flexible 2026
$240
$99
per person
Book Now
JetBlue · 5h 30m · Direct
New York
Los Angeles
Flexible 2026
$220
$89
per person
Book Now
Southwest · 4h 15m · Direct
Chicago
Los Angeles
Flexible 2026
$240
$99
per person
Book Now

Travel Protection & Compensation

Flight delayed? Cancelled? Overbooked? You may be owed up to €600. Don't travel without protection.

AirHelp

Flight Compensation

The world's largest flight compensation company. If your flight was delayed 3+ hours, cancelled, or you were denied boarding in the last 3 years, AirHelp can claim up to $650 per passenger on your behalf. No win, no fee.

  • Up to $650 per person
  • No win, no fee
  • Covers flights up to 3 years ago
  • Used by 16M+ passengers
Check My Compensation

EKTA

Travel Insurance

Comprehensive travel insurance built for event travelers. EKTA covers trip cancellation, medical emergencies, lost luggage, and event-specific disruptions. Get covered from $1.50/day — the cost of a coffee.

  • Trip cancellation & interruption
  • Medical & emergency evacuation
  • Lost baggage & delays
  • Event cancellation coverage
Get Travel Insurance

Compensair

Flight Claim Service

Compensair fights airlines so you don't have to. Their legal team handles the entire claim process — from filing to court if needed. They've recovered millions in compensation for passengers worldwide. Only 25% fee on success.

  • Only 25% fee on success
  • Legal team handles everything
  • Covers EU261 & UK261 rights
  • Average payout €350+
Claim Compensation

Did you know? Under EU Regulation 261/2004, passengers on flights to/from Europe are entitled to up to €600 in compensation for delays over 3 hours, cancellations, and denied boarding — regardless of where you bought your ticket.