We’re planning a long weekend trip to Chicago in the next few weeks (two adults, one little kid) and will be doing all of the usual stuff - Museums, Shedd, Navy Pier, and Italian Beef for breakfast, lunch, and dinner.
We’ll be booking a two bedroom AirBnB or VRBO.
I haven’t traveled to Chicago in a family-friendly context in roughly 25 years. Since then it’s been boozy overnight jaunts to the Empty Bottle or business stuff downtown.
I’d like to book the rental in a family-friendly neighborhood with low-key stuff to do / places to eat within walking distance. Cool boutiques, record stores, restaurants, vintage shops, etc. All of the normal hipster junk.
Where are the cool 35-45 year old kids in Chicago living these days?
Wicker Park, Bucktown, and Logan Square are all hipster. Humbolt Park is almost there, but I’d say it’s not ready for tourists just yet.
But from your description, I don’t think you want hipster, I think you want full-on urban gentrified neighborhoods. Lakeview and Lincoln Park are what you are looking for. Both of these neighborhoods are convenient to downtown by public transportation or car.
Someone will come along and say Bridgeport. Do not listen to them. It is a hipster neighborhood, but I would not recommend it to a tourist. It’s safe, it’s completely safe, my advice has nothing to do about crime. But you don’t go to Bridgeport for the culture or experience.
If you really want a quirky fun neighborhood that’s off the beaten path, I’d recommend Rogers Park or Edgewater. They’re convenient to Evanston, but they are far away from downtown. Though I love them, they’re probably not really suitable for you if you’re doing the downtown tourist stuff.
Rogers Park and Edgewater may not be convenient to downtown, but they’re only an hour away from there. There’s Andersonville, and also all along Devon and all along Broadway are all the authentic adventurous restaurants featuring Indian, Pakistani, Nepalese, African, and Asian/Vietnamese. Some of these restaurants have been featured on the Food Network, such as Sun Wah Barbeque, Sabri Nihari, and my favorite Anthony Bourdain pitstop, Tank Noodle. Also, there’s a slew of vegetarian restaurants, if that’s your hipster thing.
Lincoln Square is pretty much “old millennials/young Gen X with kids” central. Pretty much everything on your list right there, and convenient to the Brown Line to get downtown.
I’d agree with Wicker Park/Bucktown. Sounds like you’ll find what you’re looking for around the Damen Blue line stop.
The main difference between the Lakeview/Lincoln Park and WP/Bucktown at this point is fashion sense. More skinny jeans and tattoos in WP/B, but also tons of baby strollers and new construction, multi-million dollar, single family homes.
Warning, Chicago is one of the most unfriendly cities in the US for Air BNB. It’s really tough to find a legitimate one in a good neighborhood. ‘Registration pending’ means it’s not legally approved. This caused a true shitstorm in my building near Wrigley Field during the Cubs World Series run and there is now a no air BNB clause in my lease.
This isn’t a political thread but air BNB often serves as a scapegoat in Chicago politics for rising rent and gentrification.
To answer your question, you really might want to consider a Loop or a River North hotel to do the typical tourist stuff as there just not much residential housing there. If you’re dead set on Air BNB, Lakeview or Lincoln Park would meet your needs, although parts of Lakeview are in the Wrigley and Boystown area, which have a lot of nightlife. Wicker Park/Logan Square certainly have their hipsters, there’s no shortage of man buns there, but it isn’t the most convenient location for tourism. It’s much easier going north/south where you have both the red and brown lines, as well as the purple line express during certain hours.