Autumn is calling, and RST puts you within easy reach of three unbe-leaf-able destinations for chasing fall colors: Chicago, Denver, and Boston. Whether it’s an urban color burst along Lake Michigan, the golden aspens of Colorado, or New England’s famous fiery display, here’s what to know for perfect timing and savvy trip planning.
Photo credit: Iryna Olkhava
Chicago: Urban Vibrancy & Lakeside Splendor
Enjoy a big-city getaway during the Chicago’s most colorful time of year, when the leafy boulevards are framed on one side by a dazzling skyline and on the other by the beauty of Lake Michigan. Think lakefront strolls and photo ops in Grant Park with the cityscape as your backdrop. In the heart of the city, visit Millennium Park, or trek a few miles north to Lincoln Park or a few miles south to Jackson Park. If you’ve got a little more time, venture out to the Chicago Botanic Garden in Glencoe or the Morton Arboretum in Lisle.
Travel time: Get to Chicago on an 80-minute direct flight.
When to go: The second and third weeks of October are estimated to be perfect timing for leaf-peeping in Chicagoland.
Weather: October brings cool, crisp and dry weather. The very definition of sweater weather!
- Expect average high temps in the mid-60s and lows in the mid-40s.
- October is one of the driest months in Chicago, with only 2 to 3 inches of rain expected. Enjoy predominantly sunny or partly-cloudy skies.
Vibe: Equal parts big-city buzz and autumn calm. Perfect for pumpkin lattes at cozy cafés and scenic walks.
Other fall highlights (if you need more convincing):
- 2025 Bank of America Chicago Marathon (Sunday, Oct. 12, 2025)
- Chicago International Film Festival (Oct. 15 – 26, 2025)
Photo credit: jc_design
Denver & the Rocky Mountains: Majestic Colors & Mile-High Views
A fall vacation in Denver and the nearby Rocky Mountains will tick the boxes for those looking for laid‑back city‑meets‑mountain energy. The Mile High City’s vibrancy and views make it the ideal place to enjoy autumn – or the perfect place for launching forays into the nearby Rocky Mountains.
Travel time: Get to Denver in about 4 1/2 hrs with a short layover in Minneapolis or Chicago.
When to go: Colorado offers one of the longest fall color seasons thanks to its elevation variety.
- If you’re sticking to Denver proper, peak colors will hit in early to mid-October.
- At higher-elevation destinations within 90 miles of Denver (like Breckenridge and Estes Park), peak fall colors generally occur earlier, from mid-September to early October. (Peak colors can vary significantly based on the specific location and the year’s weather conditions.)
Weather: Denver is typically hoodie‑weather territory this time of year. If you head up into the Rockies, it’s unquestionably coat-weather.
- Expect average highs in the upper-60s in Denver, dipping into the low-40s at night. In the mountain towns, daytime highs are often in the 50s with nighttime lows near freezing.
- October is one of Colorado’s sunniest months, with low humidity and fewer rainy days. You can count on bright blue skies and crisp air.
- A surprise early snow dusting in the mountains isn’t uncommon this time of year!
Vibe: Crisp mornings and alpine vistas. Perfect for morning hikes and evenings around a fire.
Other fall highlights (if you need more convincing):
- Denver’s Oktoberfest (Sept. 19 -21 and Sept. 26 – 28, 2025)
- Breckenridge’s Craft Spirits Festival (Oct. 3 – 5, 2025)
- Estes Park’s Elk Fest (Sept. 27 – 28, 2025)
Photo credit: Sean Pavone
Boston: Fiery & Fantastic
Boston ripples with fall energy when its historic streets are lined with leaves of fiery red, smoky orange and antique gold. With historic charm at every turn, the city is both a cultural getaway and a color-seeker’s paradise. The Boston Public Garden, the Esplanade, and Boston Common showcase brilliant foliage, while nearby sites like Cambridge and the Charles River offer even more fiery views.
Travel time: Get to Boston in about 4 ½ hours by connecting in Chicago or Minneapolis.
When to go: Boston’s peak fall colors typically arrive in mid-to-late October, especially around Columbus/Indigenous Peoples’ Day. If you venture west toward the Berkshires or north toward New Hampshire, peak colors can arrive earlier (late September to early October).
Weather: Brisk and bright.
- Expect average highs around 60 to 64 degrees and lows in the mid-to-upper 40s.
- October brings a mix of crisp sunshine and occasional clouds, with around 3 to 4 inches of rain across the month.
- Breezy afternoons make for picture-perfect leaf strolls, while evenings cool quickly.
Vibe: Historical charm meets cozy nostalgia. Perfect for hot apple cider and ambling through quaint cobblestone streets.
Other fall highlights (if you need more convincing):
- Head of the Charles Regatta (Oct. 17 – 19, 2025)
- Boston Book Festival (Oct. 25, 2025)
From skyline strolls to golden mountain trails to cobblestone charm, fall color is calling. Leaf your worries behind. Your perfect autumn escape is just a quick flight from RST. Book your flight today!
