Historic Route 66 Holidays

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Historic Route 66 Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
per person
7 Sept - 13 Sept
found 1 day ago
Return direct flight included
San Francisco (SFO) to St. Louis (STL)
8.2/10 Very Good! (754 reviews)
Property was clean and the staff was friendly

Reviewed on 20 Jun, 2025

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
per person
7 Sept - 13 Sept
found 1 day ago
Return direct flight included
San Francisco (SFO) to St. Louis (STL)
8.4/10 Very Good! (1,000 reviews)
Room had issues. Addressed with staff.

Reviewed on 25 Jun, 2025

Moonrise Hotel

Moonrise Hotel

4 out of 5
Delmar Loop
per person
7 Sept - 13 Sept
found 1 day ago
Return direct flight included
San Francisco (SFO) to St. Louis (STL)
9/10 Wonderful! (1,759 reviews)
I love staying at the moonrise hotel Love the rooftop especially at night

Reviewed on 26 Jun, 2025

Ballpark Apartments by Barsala

Ballpark Apartments by Barsala

4 out of 5
Downtown St. Louis
per person
7 Sept - 13 Sept
found 1 day ago
Return direct flight included
San Francisco (SFO) to St. Louis (STL)
7.2/10 Good! (7 reviews)
It's a great location, right across from the Ballpark. It is a fairly spartan apartment set-up, with concrete floors.. a little surprising? Parking is on the street or in a pay lot.

Reviewed on 8 Jun, 2025

The Cheshire

The Cheshire

4 out of 5
per person
7 Sept - 13 Sept
found 1 day ago
Return direct flight included
San Francisco (SFO) to St. Louis (STL)
8.6/10 Excellent! (1,002 reviews)
Quirky property with an old English theme. A bit of a haunted house vibe. Checking in was an annoyance as we arrived at 11:45pm and the lone staff that could check us in had a car mishap on her way to work and we had to sit and wait in the lobby for more than an hour and only was able to get into the room at 1am. The staff did apologize and I understood it was out of her control but it was still annoying. The rooms were fairly clean. The staff was polite but not overly friendly.

Reviewed on 26 Jun, 2025

Top hotels in Historic Route 66

Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$253 per night from 29 Jun to 30 Jun
S$253
29 Jun - 30 Jun
includes taxes & fees
8.4/10 Very Good! (4,274 reviews)
"Good service and breakfast"

Reviewed on 26 Jun, 2025

Embassy Suites by Hilton Chicago Downtown River North
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is S$275 per night from 1 Jul to 2 Jul
S$275
1 Jul - 2 Jul
includes taxes & fees
9/10 Wonderful! (1,920 reviews)
"We especially loved the room service, but the best was the unique indoor pool!!"

Reviewed on 25 Jun, 2025

InterContinental Chicago Magnificent Mile by IHG
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$183 per night from 29 Jun to 30 Jun
S$183
29 Jun - 30 Jun
includes taxes & fees
9.2/10 Wonderful! (3,236 reviews)
"Great location"

Reviewed on 26 Jun, 2025

citizenM Chicago Downtown
See all 18,896 properties in Historic Route 66
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Historic Route 66 holiday package cost?
Our Historic Route 66 packages, which start at just S$1,718, are an easy way to save big bucks. Pick your preferred flights, hotels and rental cars to create your ideal trip.
How do I get a cheap travel package to Historic Route 66?
Book everything all in one place with our Historic Route 66 holiday packages. We have incredible bargains on hotels, flights and more that'll keep your hip pocket happy and your adventurous spirit alive. And, with more than 550 airlines and 1,000,000 properties globally to select from, you'll have the flexibility to mix and match as you please.
What are the top hotels in Historic Route 66?
If you're headed to Gillespie, you can't go past Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton. Both are excellent bases for exploring this lively Historic Route 66 city.
How far in advance should I book my Historic Route 66 holiday?
The earlier you book, the better. Airlines usually release flight tickets nearly 12 months prior to departure, and this is a fantastic opportunity to pick up some of the lowest prices. Just been told you need to take your holiday time next month? That's alright! Expedia are never short of fantastic deals to send you off on the getaway of your dreams, at a price you can afford.
What does an Expedia Historic Route 66 travel package include?
You can select from a combination of hotels, flights and rental cars. Once you've made your booking, you can add the fun stuff like activities and experiences. Want to pick your fare class? That's possible too. The choice is all yours when it comes to crafting your dream Historic Route 66 getaway.
What should I know before booking a Historic Route 66 travel package?
An Expedia travel package can be tailored to your budget and is a fantastic way to make your hard-earned dollars stretch further. How little or much you include is totally up to you. Hotels, rental cars and flights --- come up with a combination that suits your plans.
Can I choose my airline with a Historic Route 66 Expedia holiday package?
Yes, definitely. Expedia has more than 550 airline partners to pick from around the globe. With such a big range of choice, finding the perfect carrier to take you to Historic Route 66 shouldn't be hard.
If I'm not able to travel, can I cancel my Historic Route 66 holiday package?
You sure can, and we're here to help. You may be able to cancel or change your Historic Route 66 holiday package for free if you booked in the last 24 hours. However, you may be charged a fee by your airline, hotel or car rental company if you booked more than 24 hours ago. If life gets in the way of your holiday, take a look at our Customer Service Portal for more information.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.