Search Cheap Flights toHistoric Route 66
Search 400 airlines and 321,000 hotels worldwide.
Stop Planning & Start Exploring
FREE 24 hour cancellation on most flights
Historic Route 66 Flights as Low as $188
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Cheap Flights to Historic Route 66
Fall in love at first flight with your vacation to Historic Route 66 by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Historic Route 66 on Hotwire, and you’ll be up, up, and on a getaway in no time.
Because once the wheels are down in Historic Route 66, the good times start rolling. So buckle up, you’re in for a fun ride.
Frequently Asked Questions About flights to Historic Route 66
Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Historic Route 66 with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.
So all you have to worry about is where you’re headed after the CHI airport.
What is the cheapest month to fly to Historic Route 66?
Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Historic Route 66 are in August, but when you book your flight on Hotwire, savings are always in season.
How many airlines fly to Historic Route 66?
Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 10 to choose from for your flight to Historic Route 66.
What airport is best to fly into Historic Route 66?
When you’re planning your trip to Historic Route 66, convenience is the name of the game. Luckily, Historic Route 66 Enid Woodring Municipal Airport is nearby so you can deplane and get going on checking off everything on your Historic Route 66 must-do list.
How much are flights to Historic Route 66?
Got very cheap flights on your vacation itinerary? When you book your airline tickets to Historic Route 66 on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $188, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.
How to get cheap flights to Historic Route 66?
The trick to saving a stack of cash on your flight to Historic Route 66? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $188 right now, why wait?
Destination airport | O'Hare Intl. |
|---|---|
Destination airport IATA code | ORD |
Roundtrip price | $98 |
Last Minute Hotel Deals in Historic Route 66
Central Loop Hotel
"Great location. Reasonably priced for the location. Cheap room options if you don't plan to spend much time in your room"
Reviewed on May 23, 2026
Congress Plaza Hotel
"Great location. Walkable to all the downtown attractions. Historical hotel with updated rooms. Highly recommend."
Reviewed on May 23, 2026
Hotel Riu Plaza Chicago
"The room is clean. The location is great with many nice shops nearby, including the Starbucks Reserve Roastery. It’s within walking distance to Navy Pier, Willis Tower, boat ride and many other architectural marvels. The breakfast is good with some variations each day. The staff are generally friendly ..."
Reviewed on May 24, 2026
Avi Resort & Casino
"The overall resort is nice. The pool and beach areas are well maintained. The staff are nice and helpful. The smoke filled casino was bad, but maybe due to poor ventilation that could be improved. Also our king bed had kid sized pillows, so that made for an unrestful trip."
Reviewed on May 23, 2026
The Chicago Hotel Collection - Magnificent Mile
"There're bed bugs. Be careful"
Reviewed on May 24, 2026
Hotel Felix River North/Magnificent Mile
"Too small room no refrigerator no microwave over prized vallet parking when they park in open public parking space which cost less."
Reviewed on May 23, 2026
River Hotel
"Great staff at the front desk, but the hotel room overall was just ok - small and a bit old. The bedding was nice. The positive was a convenient location and good price, the drawbacks were no restaurant or bar onsite, no real lobby to lounge in. Overall ok, but not great."
Reviewed on May 23, 2026
The Aquarius Casino Resort, BW Premier Collection
"Old not updated. The comforter not changed it was used and had a stain on it. I had to sleep in a sheet because I was cold."
Reviewed on May 24, 2026
Nearby Cities
Popular Flight Routes
- Atlanta to New York
- Detroit to Las Vegas
- Dallas to Atlanta
- Dallas to Yosemite National Park
- Toronto to Edmonton
- Chicago to Tulum
- Houston to Lake Tahoe
- Chicago to Las Vegas
- Dallas to Miami
- Dallas to Lake Tahoe
- New York to Miami
- New York to Las Vegas
- Miami to Atlanta
- Minneapolis St Paul to Fort Walton Beach Destin
- Dallas to Branson
- Cleveland to Vero Beach
- Managua to Miami
- Atlanta to Boston
- Austin to Tulum
- Calgary to Vancouver