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72 Hours of Food to Convince Anyone To Move to the West Side
To truly fall in love with Chicago in a single weekend, you have to eat like you live here. This guide is my own personal weekend blueprint. If I had 72 hours to convince you to move to the West Side, these are the restaurants I'd put on the itinerary: neighborhood staples, deep-cut local gems, and the places that friends and family insist on revisiting every time they're back in town. Undeniably, there are so many other great spots nearby, but these are the meals that make the case. Welcome to my favorite argument for staying on the West Side.
10 places
Showing 10 of 10 places
Friday
If your beloved guests aren't flying in on Thursday night, they're already missing out on valuable eating time. But for the purposes of this guide, we'll start on Friday morning. First up: two cozy breakfast showstoppers.
Ann Sather only needs two words of explanation: cinnamon rolls.
Ann Sather Restaurant
Easygoing mainstay offering hearty Swedish-American breakfast & lunch standards.
Uncle Mike's Place deserves a bit more. I didn't grow up exposed to Filipino food, so my first visit changed my life. Complimentary lugaw hits the table as soon as you're seated, setting a tone that feels like a hug. I typically order the longanisa, while others in the group usually go for the steak or bangus. Nobody leaves disappointed or hungry.
Uncle Mike's Place
Cozy, no-frills American-Filipino joint serving hearty portions of all-day-breakfast fare & lunch.
Between the generous portions, cinnamon rolls, or Filipino porridge, I've intentionally skipped lunch. You'll need the afternoon to walk it all off anyway.
Whether you spent your morning with cinnamon rolls or longanisa, we're going French for dinner. Chez Poulet, the newest venture from the team behind Le Bouchon, earned a spot on this itinerary almost immediately. Le Bouchon has been my go-to birthday-and-anniversary restaurant for years so I knew I could count on its more approachable sister restaurant. When ordering: get the chicken, get the sides, get a Publican baguette and a bottle of wine. Leftovers aren't guaranteed, but I encourage everyone to take the chicken carcass home and freeze it. Future-you deserves the stock.
A note on strategy: Chez Poulet has become a neighborhood staple almost immediately. Every time I crave it on a weekend, it's a gamble if they've run out of chickens for the day by the time dinner comes. Hence, why I recommend chicken dinner on a Friday.
Saturday
Let's acknowledge the greatness, and ambition, of Friday's lineup. Saturday is intentionally a little lighter. This is the day for running around, showing off parks and shops, architecture or whatever else is on the itinerary. Start the morning at Spinning J with a breakfast sandwich and a seat at the counter if possible. The former soda fountain has preserved vintage charm, and watching the team make house sodas, floats, shakes, and palmers has always been a fascination.
Spinning J Bakery and Soda Fountain
Seasonal pies, gelato and soda-fountain classics served in quaint surrounds with vintage furniture.
For lunch, I'm taking you to Humboldt Park where the jibarito originated. While rooted in Puerto Rican culture, the sandwich itself is a product of Chicago's Puerto Rican community. The jibarito offers a small window into the history of Humboldt Park and Puerto Rican diaspora in Chicago.
Papa's Cache Sabroso
Tiny, beach-themed BYOB eatery serving up Puerto Rican fare, including jibarito & pollo chon.
Jibaritos are Chicago culinary icons alongside the Chicago dog or deep dish pizza. That said, when it comes to pizza, Craft Pizza has my heart. The thin crust, fresh ingredients, familiar faces, and competitive prices has us loyal customers. We usually swing by Mr. P Beverage Depot beforehand for a bottle of wine or pack of beer with dinner. The Devil in the White City and White Truffle Pie are our repeat orders.
- All ages
- Neighborly
Craft Pizza
Artisanal pizzas include margherita & truffle pies in a simple, brick-walled, counter-serve space.
For a nightcap, walk the block down to Division and visit Alley Cat. Their house cocktails are available by the batch, as well as a full bar inventory. I usually choose between two favorites: the Saturn when I'm in the mood for something bright and fruity, or the Girl Dinner Gibson for a savory cocktail with in-house pickle brine and a pickled pearl onion.
- Creative
- Late night
- Low-key cool
The Alley Cat Bar
Sunday
Shokolad is one of my favorite spots to round out a weekend visit because it can satisfy the sweet breakfast person, the savory breakfast person, and the person who wants both. Shokolad delivers a kind of comfort that feels like it came straight from your Ukrainian grandmother's kitchen.
Shokolad Pastry & Cafe
European cafe offering pastries, cookies & a savory breakfast/lunch menu with crêpes & pierogi.
Before dinner, make time for a martini happy hour at Queen Mary. If the patio is open, sit outside. If not, the nautical-inspired interior has cleverly designed bar seating so you can hold a conversation face-to-face. Two booths are reserved but available upon request for groups of 4+.
If not a martini, Queen Mary offers a rotating menu of complex cocktails with ingredients I am always googling at the bar. One permanent menu item is the Navy Strength Old Fashioned which, when in doubt, I order. This cocktail has a surprising ingredient list of rum and gin (no whiskey!), and was named best cocktail in Chicago by Chicago Magazine in 2024.
Queen Mary
An old-school saloon with original furnishings houses this cozy, maritime-themed craft cocktail bar.
Then we're ending the weekend at Lao Peng You. The dumplings are exceptional, broth is restorative, and the dan dan noodles offer some great Sichuan spice. My favorite dish is the pork and dill dumpling; the herby dill really comes through against the broth. I also pair this with the cucumber salad or wood ear mushroom salad as a side of something cold and refreshing.
Lao Peng You
Fresh dumpling & noodles star in traditional Chinese cooking, served at a counter in relaxed digs.