Who says budget travel can’t feel first class? If you’ve been dreaming of golden hour strolls through new cities, breezy beachfront mornings, or spa-side stays without the splurge – this is your moment. We’ve curated 20 ultra-affordable fall getaways that look and feel luxurious, with one-way flights under $150 and boutique-style hotel stays under $100/night. From quiet desert escapes to cosmopolitan long weekends, these deals bring elevated travel within reach – no platinum card required. Your chic, stress-free fall escape starts now. Let’s indulge, intelligently.
Flight Deals (Under $150 One-Way)
New York → Berlin (Norse Atlantic) – From $150 OW
Fly across the Atlantic in comfort for under $150—Berlin awaits with culture, fall beer gardens, and soft pretzel vibes.
Read More → The Washington Post
New York → London (Secret Flying deal) – From $119 OW
Yes, this is legit: nonstop JFK-to-London for $119 one-way. A spontaneous transatlantic indulgence with savvy savings.
Read More → Secret Flying deal
San Diego → Chicago – From $69
Fall in Chi-Town is magical—with fewer crowds, fall festivals, and iconic deep-dish. Frontier’s introductory launch fare means you can get there for about $69 one-way.
Read More → Frontier fares to Chicago, Austin, Salt Lake City
Cleveland → Orlando – From $19
Frontier’s cheap new fall routes include this Florida escape—for sunshine, theme parks, and golf, often under $20 one-way.
Book it here → Frontier Cleveland → Orlando
Philadelphia → Orlando – From $22
Likewise, Philly travelers can score one-way flights to Orlando starting in the low $20s—ideal for warm-shorts weather escapes.
Book it here → Frontier Philadelphia → Orlando
Savannah → Nashville – From $59
Feel the energy of Music City this fall—with Spirit’s new route launching October 9 at just $59 one-way. Great for a spontaneous weekend packed with honky-tonks and barbecue.
Book it here → Spirit Savannah → Nashville intro fares
Philadelphia → San Juan, PR – From $45
Caribbean calling? Use Frontier’s seasonal deals to fly from Philly to San Juan for under $50—latitude, palm trees, and ocean for less.
Book it here → Frontier Philadelphia → San Juan fare alert
U.S. → Mexico (e.g., Cancun, Mexico City) – Off-peak booking advice
Fall is considered an off-peak travel season for Mexico, and flight prices often drop significantly when booked a few months ahead.
Read more → Why fall means cheaper flights to Mexico
Hotel Deals (Under $100/Night)
Surf Club Oceanfront – Dewey Beach, DE – From $89/night
Steps from sand and surf, this Delaware beachfront stay under $100 lets you enjoy oceanfront breezes without Vegas prices.
Book it here → Surf Club hotel listing
Southern Oaks Inn – St. Augustine, FL – From $84/night
Explore America’s oldest city with this comfortable, affordable inn—complete with free parking and close to historic streets.
Book it here → Southern Oaks Inn listing
Magnolia Studios – Chicago, IL – From $99/night
A cozy guesthouse-style stay with kitchenette included—perfect for a longer fall visit in the city without splurging on hotels.
Book it here → Magnolia Studios listing
Hidden Pond – Kennebunkport, Maine (U.S.)
While standard nightly rates run high (over $600), their seasonal “Hotel Week” event in early November features harbor-facing options like the Yachtsman Hotel for around $99/night + taxes as part of the resort collection’s offerings
Book it here → Kennebunkport Resort Collection
C.W. Worth House B&B – Wilmington, NC
USA TODAY’s Readers’ Choice for best B&B in the country, this queen‑Anne‑style bed and breakfast delivers historic charm, farm‑to‑table breakfasts, and cozy comfort—all for under $100/night in scenic Wilmington.
Read About it → C.W. Worth House B&B recognition and romantic feel
Expert Insight: Booking Smart for Fall Travel
“Goldilocks window” for booking: Domestic flights are often cheapest 21–60 days before departure—perfect timing for fall travelers.
Read more → Washington Post travel booking strategy