A 40+ extroverted solo traveler considering a Memorial Day weekend trip to Chicago is confronting a question many solo travelers face: does traveling alone on a holiday weekend amplify loneliness, or is it better than staying home?
"I feel like everyone else traveling there would be with friends and family and worried about my feeling lonelier than usual, since I'll be one of the few riding solo," he wrote—articulating a fear that resonates with solo travelers who watch holiday weekends approach with mixed emotions.
The Holiday Weekend Paradox
Holiday weekends present a unique challenge for solo travelers. On one hand, they offer time off work to explore. On the other hand, they amplify the visibility of being alone because everyone else seems to be with someone.
The traveler's situation is common among people in their 40s and beyond: "All my friends are married w/ families, so I have no one to travel with." He has one friend in Chicago who will be around, plus younger cousins, but doesn't want to "interrupt their lives if they have things going on."
His alternative is to travel the following weekend instead—sacrificing the holiday time off to avoid the emotional difficulty of being solo among groups.
Why Holidays Hit Different
What makes holiday weekends harder for solo travelers isn't just being alone—it's the contrast with everyone around you.
On a random Tuesday in March, being solo in a hostel or restaurant feels normal. On Memorial Day weekend, when families are grilling in parks and friend groups are filling patios, being alone feels more conspicuous.
As the traveler notes: "I'm a total extrovert, but I think people would be weary of a guy traveling solo on a holiday weekend and not want to interact with me." Whether that perception is accurate or not, it creates anxiety that makes the experience less appealing.
What Experienced Solo Travelers Say
The post drew 23 comments, with experienced solo travelers offering perspective:
Holiday weekends can actually be great for solo travel. Many commented that cities on holiday weekends have festivals, events, and activities specifically designed for the holiday—creating opportunities to meet people.
Hostels and group activities help. Staying in social accommodation or booking group tours means you're around other travelers, not just family groups.
Your friend in Chicago changes everything. Having even one person to grab a meal with breaks up the solo time and provides emotional support.
Loneliness at home vs. loneliness traveling. Several commenters pointed out that staying home alone on a holiday weekend might feel worse than being alone in an interesting city with things to do.
People are less wary than you think. Solo travelers are common enough that most people won't find it strange, even on holidays.
The Honest Truth About Solo Travel and Loneliness
What this post reveals is something the solo travel community doesn't always acknowledge: solo travel can be lonely, and holidays make it worse.
That doesn't mean you shouldn't do it. Many solo travelers find holiday trips rewarding. But the pressure to pretend solo travel is always empowering and never isolating does a disservice to people honestly confronting whether they can handle the emotional reality.
For this traveler, the question isn't "will I feel lonely?"—the answer is probably yes, at least sometimes. The real question is: "Will I feel lonelier traveling solo on Memorial Day weekend in Chicago, or staying home alone while everyone I know is with their families?"
Making the Decision
Factors that might make the trip worth it: - Having a friend in the city to connect with - Being extroverted and comfortable striking up conversations - Staying in a social hostel or attending group activities - Focusing on activities that don't highlight being alone (museums, walking tours, concerts)
Factors that might make waiting better: - If holiday weekend prices are significantly higher - If the emotional toll of being alone on a family-oriented holiday feels too heavy - If the following weekend offers better weather or events - If you'd rather wait for a destination where you have more social connections
The best travel isn't about the destination—it's about what you learn along the way. And what this 40+ solo traveler is learning is that acknowledging loneliness doesn't mean you're doing solo travel wrong—it means you're being honest about the trade-offs. Whether those trade-offs are worth it depends entirely on you.
