Andersonville Cosy Evening

Andersonville$$3 hours 30 minEvening
~$100 for two
Get directions to all stops
Women & Children First Bookstore
1
Activity

Women & Children First Bookstore

Start at this iconic feminist bookstore — browse together, read each other passages, and maybe find a book to share.

$0 pp30 min5233 N Clark St, Chicago, IL 60640
Big Jones
2
Meal

Big Jones

2 min walk. Southern cooking done properly — heritage ingredients, buttermilk fried chicken, and shrimp & grits that transport you to the Low Country.

$30 pp1 hr 15 min5347 N Clark St, Chicago, IL 60640
Swedish Bakery
3
Dessert

Swedish Bakery

3 min walk. Andersonville's Swedish heritage in pastry form. Cardamom rolls, princess cake, and Swedish cookies since 1929.

$8 pp20 min5348 N Clark St, Chicago, IL 60640
Simon's Tavern
4
Drinks

Simon's Tavern

2 min walk. A bar since 1934 — famous for glogg (Swedish mulled wine) in winter and a perfectly divey atmosphere year-round. Cheap, authentic, beloved.

$12 pp1 hr5210 N Clark St, Chicago, IL 60640
79 couples completed this

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Comments

TwoTonight TeamStaffMar 2026

Andersonville is the most underrated date neighbourhood in Chicago. No crowds, no pretension, just genuinely great spots.

Total (for two)~$100
Duration3 hours 30 min
Best For

Couples

Best Time

Weekend

Tags

Best Seasons

All Year

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