Restaurant Suggestions for a First Date in Chicago

Anne Chekal
Chicago is a town of good eating and good drinking, and is chock full of excellent restaurants perfect for first dates. All dates are exciting, but first dates have an especially high level of intrigue and anticipation that call for the perfect setting. Though different in atmosphere, cuisine, and location, these three restaurants are excellent first date sites in Chicago.

For trendy and delicious Latin cuisine, try Cafe 28.

Cafe 28 (1800 W. Irving Park Rd, 773-528-2883.) specializes in Cuban and Mexican food guaranteed to make your mouth water. Cafe 28 is situated beneath the El tracks in the Ravenswood neighborhood with divine mojitos, green tamales, and pork dishes. Reservations not accepted for tables smaller than 6, so be prepared to be patient and spend time at the bar on Saturday nights. However, the atmosphere has the right level of noise to allow yet not require a running conversation, and has an upbeat ambiance. Expect to spend at least $60 during the evening. On-street parking is relatively available, and the restaurant is easily accessible off of the Irving Park stop on the Brown Line.

For those looking to spend time downtown, try Artopolis.

Artopolis Bakery Cafe & Agora (306 S. Halsted St., 312-559-9000) in Greektown serves delicious Mediterranean food. Artopolis has counter service during the day, but table service for dinner with an array of traditional and unexpected Greek foods. Share a pizza cooked in the wood-burning oven, and admire the shelves of edible items available for purchase while you wait. The lemon soup and almond cookies alone are worth the trip and the array of desserts in the bakery are to-die-for good. The atmosphere is casual, but so is the price, which makes it an unassuming choice for a first date of good food and people watching. Parking can be challenging so take a cab or the El (Blue line stop UIC/Halsted); no reservations. The Artopolis kitchen is open 9 a.m. to midnight.

For a no-pressure, music-filled evening, dine at Heartland Cafe.

The Heartland Cafe (7000 N. Glenwood Ave., 773-465-8005) is a Rogers Park neighborhood institution. The ambiance has a distinctively laid back and socially conscious flare, with local artist exhibits and crunchy food. If you're in a hurry, the Heartland is not the right place to be, but for an evening of relaxing conversation and music it is ideal. Live music and open mic Thursday through Sunday; covers in these instances range from $6-10/person. The Heartland is open late and after 10 p.m. half of the tables convert to open floor space for milling about or dancing. An evening at the Heartland definitely won't break the bank and no reservation needed. On-street parking available, and a free lot; easily accessible to the Red Line Morse stop.

And for the first date that goes exceptionally well, a couple can continue their time with breakfast at Tre Kronor.

Tre Kronor (3258 W. Foster Ave., 773-267-9888) is a small Scandinavian restaurant in the North Park neighborhood with amazing Swedish pancakes with lingonberries, quiche and coffee. Though a CTA bus stops nearby, diners with their own transportation will find it easier to get to the restaurant. Breakfast starts at 7 a.m. Monday through Saturday and at 9 a.m. on Sunday. Tre Kronor is best known for its breakfast and brunch, but serves lunch and dinner as well. In warm weather, sit outside in the tree-filled backyard for a romantic meal.

Any of these restaurants will be sure-fire culinary hits to set a date's tone.

Published by Anne Chekal

I am a professional writer working in the nonprofit field.  View profile

3 Comments

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  • janet Trieschman11/1/2007

    Great ideas, I can't even imagine having to afford dating these days!

  • jennybeans10/18/2007

    Great ideas for singles dating in Chicago.

  • Carol Bengle Gilbert10/18/2007

    These sound yummy.

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