Planting calendar
May Planting Guide for Chicago Gardens: Raised Beds, Containers & In-Ground
In May, Chicago gardeners can confidently plant warm-season vegetables and flowers outdoors in raised beds, containers, and in-ground gardens. This is the ideal time to transplant seedlings started indoors and sow heat-loving crops directly. Protect young plants from any late cold snaps and ensure consistent watering as temperatures rise.
Plant now (quick list)
Tomatoes, Peppers, Eggplants, Beans (bush and pole), Cucumbers, Squash (summer and winter), Corn, Herbs (basil, oregano, thyme)
Plant now
- Tomatoes
- Peppers
- Eggplants
- Beans (bush and pole)
- Cucumbers
- Squash (summer and winter)
- Corn
- Herbs (basil, oregano, thyme)
- Marigolds
- Zinnias
Start indoors
- Fall broccoli
- Cabbage
- Cauliflower
- Brussels sprouts
- Kale
- Collards
- Celery
- Leeks
Avoid
- Potatoes (plant earlier in spring)
- Peas (too warm now)
- Spinach (bolts in heat)
- Lettuce (bolts quickly)
- Broccoli (direct sow now, but better indoors for fall crop)
- Root crops like carrots (can be sown but watch for heat stress)
- Frost-sensitive seedlings without protection
- Overcrowding plants
- Waterlogging soil
- Transplanting seedlings during heat of day
Next 2 weeks
- Harden off indoor seedlings before transplanting
- Mulch around plants to conserve moisture
- Monitor for pests like aphids and flea beetles
- Stake tall plants like tomatoes and beans
- Continue direct sowing beans and cucumbers
- Water deeply early in the day
- Thin seedlings for proper spacing
- Add balanced fertilizer to raised beds
- Watch for late frost warnings
- Rotate crops to prevent soil diseases
FAQs
Can I plant tomatoes directly in the ground in May in Chicago?
Yes, after the last frost date in mid-May, tomatoes can be transplanted outdoors safely in Chicago.
Should I start seeds indoors or buy seedlings for May planting?
Starting seeds indoors 6-8 weeks before transplanting is ideal for many warm-season crops, but buying healthy seedlings is a convenient alternative.
How often should I water raised beds and containers in May?
Water deeply 2-3 times per week, adjusting for rainfall and temperature; containers typically need more frequent watering than in-ground beds.
What are the best herbs to plant in containers in May?
Basil, oregano, thyme, and chives thrive in containers and warm May temperatures.
How can I protect young plants from late frost?
Use row covers, cloches, or bring containers indoors overnight if frost is predicted.
Next steps
Get a personalized planting plan
Answer a few questions and generate a plan for your exact location and setup.
Build your garden shopping list
Get a starter kit checklist for what you want to grow (with optional links).
Ask GrowGardens AI
Get quick answers and next-step guidance for your garden.
Want this page for a different city? Try the tool and enter your ZIP: Plant this month.