Highwood feels compact, where foot traffic meets quiet streets.
Best Stays by Sonder Highwood
Find places to stay in Highwood. Choose from apartment-style stays and boutique hotels for weekend breaks, business trips, and longer city stays.
Travelers
Small-footprint, walkable, quietly social.
Highwood feels compact and close-knit, with a downtown rhythm shaped by rail arrivals, evening meals, and easy streets that give the city a distinctly local pulse.
What Makes Highwood Highwood
- Green Bay Road tables
- Downtown made for walking
- Independent kitchens, close together
- Rail-side city-center energy
- Late-night neighborhood meals
- A compact, lived-in pace
Where to Stay in Highwood
Highwood Popular Stays
Choose your perfect stays
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Good for the Weekend
Easy in-and-out for quick Highwood gateway.
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Work-friendly stays
Desks, fast Wi-Fi, and a kitchen for work trips that run long, with dinner a short walk away.
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Downtown strolls, dinner, and easy nights.
Walkable, food-led, and easy to settle into, Highwood feels relaxed, local, and best explored on foot at a leisurely pace.
Known for
A compact North Shore base with an easygoing downtown, neighborhood restaurants, and a local calendar that gives the place a small-city feel without losing its everyday pace.
Best for
Best for food-led stays, short work trips that spill into a weekend, and travelers who want a quieter home base with quick access to the surrounding suburban grid.
Walkability
Most naturally explored on foot around the downtown core and Metra station area, where errands, meals, and the day’s stops stay close together.
Closest airport
O'Hare International Airport (ORD), to the southwest.
Ideal trip length
One to two nights fits the rhythm well, with enough time to settle in, explore the center, and use Highwood as a low-key base.
Vibe
Compact, local, unhurried, practical, neighborhood-forward
What stays with you in Highwood.
Some moments feel more Highwood than others, the everyday rituals behind the things to do in Highwood.
Start your morning at a neighborhood café
Begin with coffee and a pastry in Highwood, where a small café stop turns into an easy start before the day picks up along nearby streets.
Stroll the downtown blocks for a midday break
Take an unhurried walk through Highwood's downtown, pausing at storefronts, crosswalks, and casual lunch spots that give the neighborhood its daily rhythm.
Pick up dinner from local takeout counters
Choose a simple weeknight meal from Highwood eateries, then carry it home for a relaxed dinner without leaving the neighborhood.
Unwind with an evening walk after supper
Head back out for a quiet loop along local sidewalks, watching the streets settle and the neighborhood ease into the night.
Seasons that shape Highwood’s pace.
Many travelers come in September and October for the Great Highwood Pumpkin Festival and crisp downtown walks.
Spring
Spring in Highwood feels freshly awake, with lighter foot traffic on the main streets and more time spent outside between cafés and storefronts. The pace is easy and social, shaped by longer daylight and the first return of patio tables.
Summer
Summer brings an easy, late-evening rhythm to Highwood, when dinner stretches out and the streets stay active after dark. The compact downtown feels made for drifting from one restaurant or bar to the next without much planning.
Fall
Fall gives Highwood a sharper, more settled feel. Daytime errands, coffee stops, and dinner plans fit neatly into the season’s steadier cadence, while the streets take on a quieter, more local pace between outings.
Winter
Winter makes Highwood feel compact and focused, with people moving briskly between warm interiors and short stretches of sidewalk. The season centers on restaurant tables, drink stops, and the small rituals that make downtown feel close at hand.
Annual events worth planning around
Highwood Days
A summer street festival with live music, food, and family activities across downtown Highwood.
A Taste of Highwood
A recurring summer food-and-drink festival, usually staged over several weekends.
Highwood Oktoberfest
A fall celebration of beer, food, and music, typically held in October.
Highwood Pumpkin Fest
A late-October festival with costumes, live entertainment, and seasonal activities downtown.
Local rituals, off-script.
From downtown coffee counters to late-night dinner spots, these are the Highwood places people return to between errands and evenings out.
Start the day on Highwood’s main street
Grab coffee from a small counter downtown, then watch neighbors drift in for the same easy routine before work and school.
Order dinner along the restaurant strip
Follow locals to the stretch of independent dining rooms and bars where weeknight meals turn into lingering conversations and a second round.
Wander between errands and late-night stops
Move through the walkable center for quick shopping, a casual drink, or a live-music stop, the kind of circuit Highwood regulars keep on repeat.
A few things worth knowing.
From the most walkable neighborhoods to how travelers explore the city, these notes help you plan a trip to Highwood.
Most walkable areas
Highwood's compact downtown is the easiest place to explore on foot.
Getting around
Stay on foot downtown, then use a car for trips beyond Highwood's core.
Ideal trip length
One to two nights is enough to settle into Highwood's downtown rhythm.
Good for work trips
Apartment-style stays with kitchens and fast Wi-Fi suit a work week in Highwood.
Highwood travel questions, answered.
Quick answers to the questions travelers ask most.
Highwood is walkable for everyday errands, dining, and exploring the main local streets. If you plan to move beyond the immediate area or build in time for multiple stops, a car can make the trip easier. For exact access details, check the listing and map before you book, since proximity and transit options can vary by building.
Two to three days usually gives you enough time for a relaxed visit, especially if you want to settle in and enjoy the neighborhood pace. A longer stay works well if you are mixing work and downtime or using Highwood as a quieter base. If your plans depend on location-specific conveniences, review the listing for details that may affect your stay length.
The easiest approach depends on where you are staying and where you are headed, so it helps to plan around the listing location. Walking covers a lot of the day-to-day neighborhood rhythm, while rideshare or a car may be more practical for wider local trips. If transit access matters to your stay, confirm the listing details before reserving.
Yes, Highwood can work well for a business stay if you want a quieter base with room to spread out. Apartment-style layouts are often a good fit for longer work trips, but setup and workspace features vary by property. Check the listing for desk space, WiFi details, and any building-specific amenities before you book.
Accessibility can vary by building, so the safest answer is to check each listing carefully before booking. Look for elevator access, step-free entry, and bathroom details if those features matter to your stay. If you need a specific setup, confirm the property information directly so you know what is available in advance.
Go with curiosity. Come back with stories.
The best trips rarely go exactly as planned. Sonder keeps you closer to the neighborhoods, kitchens, and small moments that make a city worth remembering.