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Eric Welander

YouTuber covering Apple and smart home for busy people
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Eric's Guide to Chicago

Eric's Guide to Chicago

I love Chicago. While in college at Wheaton, I rode Metra trains into the city to just walk all over, getting to know the streets and places. Whether it was proposing to my now-wife in 2012, living in the city in 2017, or any other year since 2007, many blocks from The Loop to Lincoln Park hold memories from different eras of my life.

As a busy, suburbanite dad, I usually find myself downtown a handful of times a year for a dinner, meeting, or weekend with my wife. 

This isn’t meant to be a comprehensive guide to everything in Chicago, but it’s a list of what I enjoy and you might too. There are many gems in the Chicago neighborhoods around downtown, but this guide focuses on the main downtown area you will probably stay in or visit as a tourist/visitor.

Things to do

  • Wendella Architecture Tour - Chicago has amazing architecture, and Wendella is THE tour company for it
  • Chicago Art Institute (art museum) - You would be surprised by the number of famous art pieces here in Chicago, not New York or Paris.
  • Chicago River Walk - a great place to walk in warmer months that leads to great parks and the biggest tourist trap of all, Navy Pier
  • Museum of Science and Industry - amazing and worth the trek south, especially with kids older than 4
  • Chicago Symphony Orchestra - one of the greatest orchestras in the world, particularly renowned for their brass section.
  • Wrigley Field - a classic place to watch the Cubs play Major League Baseball, and worth the trek north. But keep your eyes open and brain on while navigating crowds.
  • Skydeck at the Sears Tower - Now called The Willis Tower, this skyscraper has next level views that are worth the expensive trip to the top. It pairs well with the building food court or breakfast at Lou Mitchell’s.
  • Field Notes pickup - If you’re familiar with Field Notes notebooks, you can pick them up orders from the Chicago HQ in the West Loop. There’s not too much to see, but fun if you’re already a fan of Field Notes. These notebooks also make great gifts.
  • Visit Cloud Gate - Also known as "the bean". It's nothing mind-blowing, but free, fun, and convenient
  • Michigan Ave Apple Store - one of the world’s great Apple Stores…so great that John Ternus stood in front of it during the September 2025 iPhone Air introduction.
John Ternus introducing iPhone Air during Apple's September 2025 event in front of Apple's flagship Chicago store on Michigan Ave

Casual Eating Spots

Desert

  • Garrett Popcorn - Garett Mix is really good, really messy, and so worth it!
  • Stan’s Donuts - A solid donut shop, technically from LA, but very Chicago
  • Eataly - My wife and I regularly go here for cannolis on city staycations. It’s not a local Chicago spot, but it’s still great. Pick up a jar of Amarena wild cherries to take home while you are there. They make a seltzer water sweet and special.

Nice Restaurants

Booking some restaurants in Chicago might be harder to get than tickets to a Taylor Swift concert. Plan and research when and where to have a nice meal long before you arrive.

Hotels

When I book a hotel in Chicago, about an hour from my driveway, it’s using points to book a nice hotel for a night or two with my wife. I don’t always live this large with my hotel choices elsewhere.

I also like to pair nice hotels with nice restaurants. There’s nothing better than scoring a deal on a nice hotel in the dead of winter, and then going to an amazing meal without putting on a coat and going outside.

  • Park Hyatt Chicago - my favorite all-around nice hotel in Chicago
    • Uses Lutron lighting scene controls and motorized shades
    • Pairs well with NoMi restaurant above in the same building
  • The St. Regis Chicago - One of the nicest hotels I’ve ever stayed in with the best fitness center and pool a city hotel can have
    • Uses Lutron lighting scene controls
    • Pairs will with Tres Dita restaurant above in the same building
  • The Peninsula Chicago - THE nicest hotel I’ve ever stayed in and has an amazing fitness center and pool
    • Customized Android tablets control everything from lights, to TV, to the do not disturb sign
    • Pairs well with The Lobby Restaurant above as part of the hotel
  • The Ritz Carlton Chicago - amazing location for shopping, especially at the American Girl store
  • The Gwen - a very nice, smaller Marriott hotel with a great location for shopping

Working in the city

Personal retreat, getting work done on a vacation, or something in between: if you need a spot with good internet, bathrooms, and beverages for a full day of work, WeWork spots in Chicago are usually between $30 and $40 per person per day. It’s a splurge, but skyscrapers like 330 North Wabash or 1 South Dearborn are very inspiring places to get work done.

Flying From O’Hare

Chicago has two big airports, O’Hare and Midway. O’Hare (ORD) is much closer to where I live so it’s what I always fly. Coming to Chicago or just passing through, these spots will make your time in the terminal way better:

  • Tortas Frontera - In terminals 1 and 3, this is the same company behind Topolobampo mentioned in the nice restaurant section, but this time with amazing sandwiches and tortilla chips.
  • Garett Popcorn - In terminals 1, 3, and 5, it’s great popcorn to take home or to friends. If eating during your flight, be sure to spread the cheese popcorn residue all over your seat and your neighbors. Tell them it was my idea. Keep in mind that many Chicago locations pop their popcorn fresh, onsite. The ORD and similar satellite locations still have fresh popcorn, but technically not quite as fresh.

Want to meet up?

If we already know each other in real life, send me a message or email and let’s see if we can meet up? Realistically, it will be just me, not the whole family, but I love heading into the city to meet for dinner, drinks, or just a morning coffee. No promises that I'm available, but it would be fun if I am.