MEGAN'S GUIDE: CHICAGO
*Written by Chicago local, Megan. I can tell you from experience, Megan is your go-to travel girl. From my roommate living in Madrid, to traveling to Havana and Copenhagen together, she is sunshine in human form. Any recommendation of hers is guaranteed to be such a gem.
BEST TIME TO TRAVEL Late May through early October is peak Chicago — rooftops, golden hour, and the lake shimmering. But don’t sleep on December. The city knows how to do winter: cozy bars, glowing lights, and a Christmas market straight out of a snow globe.
WHERE TO STAY Stay in a boutique hotel in West Loop or Wicker Park — both walkable, full of personality, and close to the best food and nightlife. Think exposed brick lofts, skyline views, and vintage greystones with big-window reading nooks.
Favorites:
– Soho House (if you want a pool + a scene)
– The Robey (Art Deco with a rooftop bar)
– Publishing House B&B (a warm, design-forward stay in a former print shop)
friday.
Start early with a draft oat latte on the patio at La Colombe. Then hop on the Chicago Architecture River Cruise — yes, it’s touristy, but it’s iconic for a reason. Best views in the city + a deep dive of Chicago’s history.
Post-cruise, grab a glass of sauvignon blanc at City Winery on the Riverwalk and settle in for some excellent people-watching.
Choose Your Afternoon Adventure…
– Art lover? The Museum of Contemporary Art is small enough to not overwhelm, but impactful enough to stay with you all weekend.
– Need fresh air? Walk The 606, an elevated greenway through Logan Square, Bucktown, and Humboldt Park — think High Line, but more local.
– Drink with a view enthusiast? Linger downtown with a skyline cocktail at Cindy’s Rooftop.
Dinner is in the West Loop — where the restaurant scene is electric.
Book a table at Girl & the Goat for bold, inventive shared plates. No luck? Head to Mama Delia for Basque pintxos, natural wine, and sultry lighting.
Nightcap: Slide into a booth at Gilt Bar in River North. Candlelit in a Gatsby way. Order the Gilt Old Fashioned and let the city settle around you.
saturday.
Start your morning at Lula Café in Logan Square — a local favorite for organic, imaginative brunch. The ricotta pancakes? Unbelievable. Sip a lavender latte and linger on the sidewalk patio. Walk it off at the Logan Square Farmers Market (if you're here on a summer weekend).
Later, grab an oat matcha from Metric Coffee in West Fulton Market, then swing by Humboldt House for dreamy vintage and floral finds.
Dinner is at Monteverde — handmade pasta that tastes like a Roman holiday.
After dinner, catch a set at The Second City in Old Town. This is where improv legends are born (Tina Fey, Colbert — the gang’s all started here). Still got steam? End the night with a martini at The Sparrow — Havana 1930s meets Chicago cool.
sunday.
Start slow with caffeine and croissants at Sawada Coffee in West Loop. Order the Military Latte (matcha + espresso) and bask in the industrial-chic calm.
Later, round out the weekend on a walk on the Lakefront Trail. Start at Montrose Beach and head south toward Belmont Harbor — the skyline views can’t be beat. If it’s sunny, grab a lakeside picnic lunch from Foxtrot and soak it all in. Then, if shopping’s on the agenda, Michigan Avenue is unmatched (bonus points if it's spring and the tulips are in bloom!)
If you’ve got time before you leave:
– Pop into the Art Institute of Chicago. Even a quick trip through the Thorne Miniature Rooms and Chagall windows is worth it.
– Or ride up to 360 Chicago in the Hancock building for panoramic views (also, there's a bar at the top).
OTHER SPOTS NOT TO MISS…
Momotaro (elevated sushi in West Loop)
Elske (Michelin-starred, but low-key and charming)
Spilt Milk (cocktails in a vintage pharmacy setting)
The Aviary (molecular cocktail magic)
3 Arts Club Café (inside RH Gold Coast — ultimate indoor garden vibes)
LUXBAR (Gold Coast classic — get the burger)