Dogs, Sandwiches, Dinner this week

Question

Hi - we have a short time in Chicago Thursday and Friday and hoping to get a few recommendations on food. Looking for a hole-in-the wall type place for a Chicago dog and Italian Beef Sandwich for lunch each day. Suggestions for each around the Loop, Magnificent Mile and Wrigley Field greatly appreciated. Trying for family run, non-chain places but willing to go for whatever is interesting. I know they are touristy areas but would love anyone’s top tips.

Also looking for an Italian restaurant for dinner Thursday night. Hoping for nice, authentic pasta dishes for around $30/plate plus apps and wine ($40-50ish/bottle). Something we can get into with late notice - 2 late 30’s somethings.

Thank you very much!

Answer

Chicago is famous for its hot dogs and Italian beef sandwiches, and there are some great family-run or iconic local spots near the Loop, Magnificent Mile, and Wrigley Field where you can get authentic versions without stepping into a chain restaurant.

For Chicago-style hot dogs:

Portillo’s: While it’s a larger local chain, it started family-run and is iconic. There are locations near the Magnificent Mile and downtown; classic Chicago dogs are a must.
Superdawg Drive-In: A retro-style, family-run drive-in located a bit west of the Loop. Famous for Chicago dogs, served with their signature pickles and fries.
Gene & Jude’s: Near the western side of the city, considered one of the best Chicago hot dog experiences. Minimalist, casual, and extremely popular for locals.
Chicago Dogs on Wrigley Field day: You can grab a classic Chicago dog from Wrigleyville vendors just outside the stadium before or after a game.

For Italian beef sandwiches:

Al’s Beef: Near the Loop and Magnificent Mile. Family-run, classic Italian beef, dipped in gravy or “au jus,” with giardiniera toppings available.
Buona Beef: A local chain but still very authentic; the Chicago-style beef sandwich is excellent. Locations in downtown and surrounding areas.
Johnnie’s Beef: Known for tender Italian beef and great sandwiches; smaller locations near downtown make it easy for lunch on the go.
On Wrigley Field day: You’ll also find Italian beef vendors in the Wrigleyville area, though lines can be long during game days.

For Italian dinner on Thursday night:

RPM Italian: Near River North, modern and sleek but offers high-quality pasta dishes, apps, and wines around your budget. Late-night reservations are sometimes possible.
Osteria Langhe: In Logan Square area, family-run and serves authentic Northern Italian dishes. Cozy, slightly off the main tourist track but excellent for pasta and wine.
Piccolo Sogno: River North location, well-known for fresh, handmade pastas, wood-fired meats, and reasonably priced wines. Can often accommodate last-minute diners at the bar or outdoor seating.
Via Carducci: Near downtown, smaller and authentic Italian, with pasta specials and good wine selection, fits your $30–40 per plate budget.

Tips:

For lunch, try to go slightly before or after typical lunch hours (11–11:30am or after 1:30pm) to avoid lines.
For dinner, call early in the day to check if they can accommodate a last-minute reservation; many Italian restaurants hold a few spots for walk-ins.
Consider using the rooftop or bar seating options at Italian restaurants if dining at peak evening hours for easier access.

With this mix, you’ll experience authentic Chicago-style hot dogs and Italian beef sandwiches during the day, and enjoy a high-quality Italian dinner with pasta and wine in the evening.