Planting calendar
May Planting Guide for Chicago Gardens: Raised Beds, Containers & In-Ground
May in Chicago is ideal for planting warm-season vegetables and flowers in raised beds, containers, and in-ground gardens. With frost risk mostly passed, you can safely transplant seedlings and sow seeds directly outdoors. Focus on heat-tolerant crops and continue nurturing early spring plantings.
Plant now (quick list)
Tomatoes, Peppers, Eggplants, Beans (bush and pole), Cucumbers, Zucchini, Herbs (basil, parsley, dill), Marigolds

Plant now
- Tomatoes
- Peppers
- Eggplants
- Beans (bush and pole)
- Cucumbers
- Zucchini
- Herbs (basil, parsley, dill)
- Marigolds
- Sunflowers
- Sweet corn
Start indoors
- Winter squash
- Pumpkins
- Melons
- Brussels sprouts
- Broccoli (for fall harvest)
- Cauliflower (for fall harvest)
- Kale (for fall harvest)
- Cabbage (for fall harvest)
- Celery
- Leeks
Avoid
- Potatoes (planting late May can reduce yield)
- Peas (best planted earlier in spring)
- Spinach (bolts quickly in heat)
- Lettuce (bolts quickly in heat)
- Radishes (bolts quickly in heat)
- Early corn varieties (may mature poorly if planted late)
- Delicate cool-season flowers
- Root crops sensitive to heat (carrots, beets)
- Overcrowding seedlings
- Planting without soil warming
Next 2 weeks
- Harden off indoor seedlings before transplanting
- Mulch around plants to retain moisture
- Monitor for pests like aphids and flea beetles
- Water consistently, avoiding overhead watering
- Support tall plants with stakes or cages
- Thin seedlings if overcrowded
- Fertilize containers and raised beds as needed
- Remove early weeds to reduce competition
- Watch for late frost warnings
- Harvest early crops like radishes and greens
FAQs
Can I plant tomatoes directly in the ground in May in Chicago?
Yes, by mid-May soil temperatures are warm enough to transplant tomato seedlings outdoors safely without frost risk.
Should I start seeds indoors or plant directly in May?
Warm-season crops like beans and cucumbers can be sown directly, but starting melons and winter squash indoors improves success.
How often should I water raised beds and containers in May?
Water daily or as needed to keep soil consistently moist, especially in containers which dry out faster.
What are common pests to watch for in May?
Aphids, flea beetles, and cutworms become active; inspect plants regularly and use appropriate controls.
Is it too late to plant cool-season crops like lettuce in May?
Lettuce and other cool-season crops tend to bolt quickly as temperatures rise, so it's better to focus on heat-tolerant plants now.
Next steps
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