Every Chicago cook spends August pretending the tomatoes at the store are fine. They are not fine. Then one Saturday in late summer a market table shows up piled with lumpy, split, sun-warm heirlooms that smell like the vine they came off, and you remember what the fruit is supposed to taste like. That window lasts about five weeks. This is the dinner party to spend it on.
The three course tomato dinner party menu
The rule is the same one behind the strawberry menu from June: pick the one ingredient the season is shouting about and let it carry the night. Tomatoes are easier. They need salt, oil, and about eleven minutes of your attention.
First: the tomato plate. Two or three heirlooms in different colors, sliced thick, laid out on your biggest board with nothing on top but flaky salt, your best olive oil, and torn basil. Scatter a few halved cherry tomatoes for contrast. Put a loaf of good bread next to it and let people build their own. This course takes six minutes and gets more compliments than anything you will cook all year, which tells you something about cooking.
Main: blistered cherry tomato and sausage skillet. One pan, fennel sausage, three pints of cherry tomatoes cooked until they collapse into their own sauce, white beans, a handful of greens at the end. Full recipe card below. It is loud, it is red, and it feeds six without anyone standing at the stove after the guests arrive.
Last: not tomatoes. Two courses of one fruit is a theme. Three is a bit. Buy an olive oil cake from a bakery you like, serve it with cold whipped cream, and add a spoon of the tomato jam below if you want to be a show-off. Skip the jam if you don't. The cake will be gone either way.
Blistered Cherry Tomato and Sausage Skillet
Ingredients
- 1 1/2 lb fresh Italian sausage, sweet or hot, casings removed
- 3 tbsp olive oil, divided
- 3 pints cherry or Sungold tomatoes, about 2 1/2 lb
- 4 cloves garlic, sliced thin
- 1 tsp fennel seed, crushed (optional)
- 1/2 tsp red pepper flakes
- 2 cans (15 oz each) cannellini beans, drained and rinsed
- 1/2 cup chicken stock or water
- 4 cups baby spinach or chopped chard
- 1/4 cup grated Parmesan, plus more for the table
- Kosher salt, black pepper, torn basil to finish
Method
- Heat 1 tbsp oil in a wide skillet over medium high. Brown the sausage in large crumbles, 6 to 8 minutes. Move it to a plate.
- Add the remaining oil and all the tomatoes. Leave them alone for 3 minutes so they blister and split. Stir, add the garlic, fennel seed, and pepper flakes, and cook 5 more minutes, until about half the tomatoes have collapsed into sauce.
- Add the beans, stock, and sausage. Simmer 8 to 10 minutes until glossy and saucy. Season with salt and pepper.
- Stir in the greens until just wilted, then the Parmesan. Finish with basil. Serve from the skillet with bread and extra cheese, and let people fight over the crusty bits.
Tomato jam for show-offs
Halve a pound of cherry tomatoes and simmer with a third of a cup of sugar, a tablespoon of lemon juice, and a pinch of salt for about 25 minutes, until it coats a spoon. Cool. Keeps a week in the fridge and makes the olive oil cake look intentional.
The shopping list and the only rule that matters
Buy tomatoes the day before or the day of, and never put them in the refrigerator. Cold kills the exact flavor you paid for. Leave them stem side down on the counter. Everything else on the list is pantry: olive oil, beans, stock, a wedge of Parmesan. If your kitchen is missing a wide skillet or a board big enough for the tomato plate, the essentials post sorts what is worth owning from what is not.
Where Chicago hosts shop for a tomato dinner party
Green City Market in Lincoln Park runs Wednesday and Saturday mornings at Clark and Lincoln, and the tomato tables there in September are the best in the city. Go early, buy the ugly ones (the splits and the cracked shoulders are the ripest), and ask the farmer which variety peaked this week. The West Loop market on Monroe runs Saturdays if that side of town is closer. Logan Square Farmers Market on Sundays is the other reliable move, and it comes with breakfast. Skip anything sold in a plastic clamshell. You can taste the difference before you pay.
A ripe tomato is a deadline. Set the date before it passes.
So set it. Pick a Saturday in the next few weeks, hit the market, and cook the one pan. Six people, one skillet, one loaf, and the last warm night you will get before the lake wind turns. Put the date somewhere real, with a guest list and a plan, and the tomatoes do the rest. One good night buys the next.