Holiday Weekend Event Rentals in Chicago: Book Early

If you host on a normal Saturday in June, you compete with weddings. If you host on the Saturday of a long holiday weekend, you compete with weddings, graduation parties, family reunions, block parties and every backyard in Chicagoland. The rental companies only have so many trucks, so many crews and so many tables. Those weekends fill up.

This guide explains why, how the schedule works when the Monday is a holiday, and what to do to get what you want. It pairs well with our guides on peak-season event rentals in Chicago and Fourth of July backyard party rentals.

Why holiday weekends sell out

Three things stack up.

• Everyone wants the same days. The Saturday, Sunday or the holiday itself are the favorites. A rental company can only deliver so many orders in a day.
• Stock is fixed. A company that owns 400 chairs cannot rent 600. Tents are scarcer still, because each one needs a crew and a truck.
• Long weekends take a day away. A rental company has fewer working days to get everything out and back. If the Monday is a holiday, many are closed or running a short schedule, so the Tuesday becomes the big pickup day.

Delivery and pickup on a holiday weekend

On a regular weekend, many rentals go out Friday and come back Monday. On a long weekend, the pattern changes.

• Delivery is often Thursday or Friday. Some companies add a Wednesday option for tents.
• Pickup is often Tuesday, not Monday, because the Monday is a holiday.
• Windows are wider. You may get a 4-hour delivery window rather than a one-hour slot. Fit your setup around it.
• Fees can change. Some companies charge more for holiday delivery or for any pickup on the holiday itself. Ask for the fee in writing. Our guide to event rental delivery fees shows what drives them.

Since the items stay with you for about 4 days, you need a place to keep them dry and safe. Stack chairs in a garage and keep linens off the grass. Rain can come on any of those days, and wet linen is a charge on a damage waiver. See damage waiver explained.

When to book

These are rules of thumb. Peak weekends can sell out earlier in a busy year, and smaller orders are easier to place than big ones.

If you have a flexible date, ask what is open on the Sunday or the Friday. A Sunday party on a holiday weekend often has more availability than the Saturday. A tent for July 4th is the hardest item, so start there.

Bundle the order

Splitting one party across three rental companies means three phone calls, three delivery windows and three Tuesday pickups. On a holiday weekend, that is where things go wrong. One late truck leaves you with tables and no chairs.

We help Chicago-area hosts plan and book chairs, tables, linens, dinnerware, tents, heaters, lighting and games from established rental companies. You get one quote and one person to deal with, and we check your date with the rental companies. Our fee is 10% on top of the rental company's price and it is already included in the prices on the site.

If you are not sure what you need, start with the rental order calculator and the backyard party planning kit.

What most hosts find out too late

• The rental company may close on the holiday. Many shut Memorial Day, July 4th and Labor Day, or run a skeleton crew. If you need a pickup on the holiday itself, that can cost extra or not be possible.
• Alley and street access is harder on a holiday. Chicago block parties, parades and street closures can block the truck. Tell the rental company about alley garages, narrow gangways and any street closed on your block. See alley deliveries.
• Count everything at delivery. Count chairs and tables when the crew drops them off, not on Tuesday. A short count is easy to fix on Thursday and hard to fix after the party.
• Heaters need fuel. Propane may not be included. Ask before you assume. This matters most for a cool Labor Day evening.
• Measure doors and stairs. If your tables have to go up a flight or through a narrow gate, a 6-foot table will not turn a tight corner.

Weather across the three weekends

• Memorial Day can still be cool in Chicago. A heater or a jacket plan is smart for the evening.
• July 4th is hot, with storms in the forecast some years. A tent helps for both shade and a pop-up shower. See heat plan for Chicago summers.
• Labor Day can be warm in the day and cool at night, and sunset comes earlier than in July.

A short checklist

Get your holiday weekend on the calendar

Book a free 15-minute planning call and we will help you list what you need, pick a delivery day and check availability. Or get a quote with your date, guest count and address. One call covers the whole rental list.