The Jewish High Holidays are not one meal. In 2026 they are a two-week span containing at least four distinct catering decisions, two of which fall on the same weekend, one of which cannot receive a delivery at all, and one of which has to be ready to eat the minute the door opens after nightfall. Households that treat the season as a single dinner spend September improvising. Households that map it in August do not.
What follows is the 2026 Chicago calendar with the timing that actually governs delivery, the order in which decisions should be made, and the point in the season at which flexibility starts to disappear.
Start planning your High Holiday catering with our team.
This guide is for planning the full High Holiday calendar: booking windows, meal counts, delivery timing, and the order in which to make decisions. For current menus, availability, and ordering, use the Rosh Hashanah catering page or Yom Kippur break-fast catering page.
The 2026 Calendar, With the Timing That Matters
Jewish holidays begin at sundown, which means the calendar date on your phone is not the deadline. Candle-lighting and nightfall times below are computed for Chicago coordinates and follow the common eighteen-minute convention. Communities vary, so confirm against your own congregation.
Rosh Hashanah 5787
- Erev Rosh Hashanah: Friday, September 11, 2026. Chicago candle lighting approximately 6:48 pm. The first festival dinner is this evening.
- Rosh Hashanah day 1: Saturday, September 12. Second-night candle lighting approximately 7:47 pm, and the second festival dinner follows.
- Rosh Hashanah day 2: Sunday, September 13. The holiday ends at Havdalah, approximately 7:45 pm.
Yom Kippur
- Erev Yom Kippur, Kol Nidrei: Sunday, September 20, 2026. Chicago candle lighting approximately 6:33 pm. The pre-fast meal, the seudah mafseket, is traditionally eaten in the afternoon and finished before that time.
- Yom Kippur: Monday, September 21. The day is spent in synagogue.
- The fast ends at nightfall Monday, September 21, Havdalah in Chicago approximately 7:31 pm, roughly twenty-five hours.
Sukkot follows immediately
- Erev Sukkot: Friday, September 25. Sukkot days one and two, Saturday September 26 and Sunday September 27.
The 2026 Detail That Changes Everything: Day One Falls on Shabbat
In 2026 the first day of Rosh Hashanah falls on Shabbat, Saturday September 12. For observant households that creates one continuous stretch from Friday sundown through Sunday nightfall in which there is no cooking, no shopping and no receiving deliveries.
The practical consequence is precise:
- Everything for both Rosh Hashanah dinners has to be received before approximately 6:48 pm on Friday, September 11.
- The next possible delivery is after nightfall on Sunday, September 13.
- Second-night dinner therefore has to be food that was already in the house on Friday afternoon and holds well, or a menu built to be reheated where reheating is permitted for the household.
- In many communities the shofar is sounded only on day two, Sunday September 13, because day one is Shabbat.
If you plan nothing else early this year, plan to have any required deliveries completed before Friday evening on September 11, subject to the current service options the team confirms. That single decision removes the most common High Holiday failure.
The Order of Operations: What to Decide, and When
Work the season as a sequence rather than a to-do list. Each step depends on the one above it.
1. Count the meals, not the holidays. For 2026 a full-season household is planning up to four: Rosh Hashanah first-night dinner, Rosh Hashanah second-night dinner, the pre-fast meal on Sunday September 20, and the break-fast on Monday September 21. Add Sukkot if you host it. Deciding this first is what makes every later step answerable.
2. Fix the guest count for each meal separately. They are rarely the same number. Rosh Hashanah dinners tend to be seated and countable. Break-fast is the least predictable headcount in the season, because families arrive as units and plans shift after Neilah. Set a realistic ceiling for each.
3. Decide service style per meal. Rosh Hashanah dinners are seated events and can be plated, family style or buffet. The pre-fast meal is traditionally simple and moderate. Break-fast is a buffet by nature, because guests arrive together and need to be served immediately. Service style, more than menu, determines what the meal requires of you.
4. Decide delivery or full service per meal. Ready-to-serve delivery suits break-fast and the pre-fast meal, because both are designed to be set out without cooking. Seated Rosh Hashanah dinners for a larger group are where on-site service starts to change the evening. These are two different models and are quoted differently.
5. Choose dairy or meat per meal and state it. Rosh Hashanah dinners are traditionally meat or pareve. Break-fast tables are traditionally dairy, which is why bagels, spreads, smoked fish and kugel dominate. Households that keep meat and dairy separate should not receive a mixed table, and telling guests which it is prevents questions at the door.
6. Collect dietary needs in the invitation. Ask for allergies, vegetarian, vegan and gluten-sensitive needs ten to fourteen days out, compile them into one list, and hand that list to your caterer with the order rather than the week of.
7. Confirm delivery windows in writing. For 2026 the two that matter most are the Friday September 11 pre-sundown window and the Yom Kippur staging window on Sunday September 20. Get both on paper.
8. Plan serviceware and seating last, but do plan them. Count serving pieces, decide between upgraded disposables and china, and seat more people than a standing reception ratio would suggest, especially at break-fast.
9. Look at Sukkot before you stop planning. Sukkot begins four days after Yom Kippur ends. Households that host during Sukkot are far better off ordering it in the same conversation than starting again in late September.
When to Book
There is no single universal deadline, and any caterer who gives you one is guessing about your event. What is reliably true is this: every caterer in the Chicago area produces the entire High Holiday season inside a handful of days, and capacity is finite. In 2026 the two heaviest production days across the market are Friday September 11 and Monday September 21.
Three practical rules follow.
- Book in the order the meals occur, but decide them together. A single conversation covering all four meals holds your production slot across the whole season instead of competing with it twice.
- Earlier bookings keep menu flexibility, not just availability. Custom items, larger formats and specific delivery windows are the first things to become unavailable, well before a caterer is fully booked.
- Headcount can move. The date cannot. Get the date, address and service window locked, then refine the count. Proposals are built from ranges for exactly this reason.
To confirm current order cutoff dates for the 2026 High Holidays, call the office directly. Published deadlines change year to year and the specific 2026 dates should come from the team rather than from a guide.
Menus: Where to Go Next
Menu planning has its own detail and its own pages.
For Rosh Hashanah, the table is built around symbolic foods: round challah dipped in honey, apples and honey, brisket or honey-glazed chicken, tzimmes, sweet kugel, honey and apple cakes, pomegranate, and a new seasonal fruit for the second night. Sephardic households may hold a Rosh Hashanah seder of simanim, symbolic foods eaten in order with blessings. Full menus and ordering are on our Rosh Hashanah catering page.
For Yom Kippur, the break-fast is dairy-forward and make-ahead: bagels with smoked fish and cream cheese, egg and tuna salads, noodle and potato kugel, blintzes, a vegetable strata, salads, and cakes with coffee. Everything is chosen because it can be eaten cold or at room temperature the moment guests arrive. Full break-fast menus and ordering are on our Yom Kippur catering page, and the break-fast menu detail and break-fast timing and setup pages go deeper.
A Note on Tone Across the Two Holidays
The two holidays sit ten days apart and ask for opposite things from a host. Rosh Hashanah is hopeful and social, and a table that looks abundant is exactly right. Yom Kippur is the most solemn day of the year, and the break-fast that ends it should feel like relief rather than an occasion. Simple abundance, quietly served, no program, nothing that asks for guests’ attention. Getting that register right matters more to how the evening is remembered than any single dish.
Traditional greetings differ too. Shanah tovah or l’shanah tovah for Rosh Hashanah. G’mar chatimah tovah before Yom Kippur, and tzom kal, an easy fast, to someone who is fasting.
Working With Catering by Michaels
Catering by Michaels has produced Chicago-area events since 1980 from the Morton Grove kitchen at 6203 Park Ave, serving Chicago and the surrounding suburbs. Because the season concentrates into so few days, it helps to raise the whole season in one conversation: your Rosh Hashanah dinners, your pre-fast meal and your break-fast together, with delivery windows discussed against sundown rather than against a clock time you pick. [Confirm which of these meals the client actually takes orders for before publish.]
To map your 2026 High Holiday meals and confirm delivery windows, call (847) 966-6555, email events@cateringbymichaels.com, or contact the Catering by Michaels team.
Frequently Asked Questions
When are Rosh Hashanah and Yom Kippur in 2026?
Rosh Hashanah begins at sundown on Friday, September 11, 2026, and ends at nightfall on Sunday, September 13. Yom Kippur begins at sundown on Sunday, September 20, and ends at nightfall on Monday, September 21. Chicago candle lighting is approximately 6:48 pm on September 11 and approximately 6:33 pm on September 20, with the fast ending at approximately 7:31 pm on September 21.
Why does Rosh Hashanah 2026 need earlier ordering than usual in the Chicago area?
Because the first day falls on Shabbat. Friday sundown through Sunday nightfall is one continuous stretch with no cooking, shopping or deliveries for observant households, so food for both dinners has to be received before approximately 6:48 pm on Friday, September 11.
How many separate meals should a Chicago household plan for the High Holidays?
Up to four: two Rosh Hashanah dinners, the pre-fast meal on the afternoon of Sunday September 20, and the break-fast after nightfall on Monday September 21. Sukkot, beginning Friday September 25, adds more for households that host it.
How far in advance should I book High Holiday catering?
Sooner than feels necessary. The whole Chicago market produces the season in a handful of days, and custom items, larger formats and specific delivery windows disappear before general availability does. Confirm the current year’s order cutoff with the office rather than assuming last year’s dates.
Can catering be delivered on Yom Kippur itself?
Plan not to need it. The day is spent in synagogue and nothing about the meal should require attention during it. The reliable approach is to take delivery on the afternoon of Sunday, September 20, stage everything before candle lighting, and have a break-fast spread that needs no cooking after nightfall. Confirm available Monday evening windows with the office.
Do I need to give a final headcount when I book?
No. Lock the date, address and delivery window first, then refine the count. Break-fast counts in particular tend to grow, so give a realistic ceiling rather than an optimistic floor.
Should the Rosh Hashanah table and the break-fast table follow the same menu approach?
No. Rosh Hashanah dinners are seated, traditionally meat or pareve, and built around symbolic foods. Break-fast is a dairy buffet built entirely around being served cold or at room temperature the moment guests arrive. They are different events with different logistics.
What is the right greeting for each holiday?
Shanah tovah or l’shanah tovah for Rosh Hashanah. G’mar chatimah tovah as Yom Kippur approaches, and tzom kal, meaning an easy fast, to someone who is fasting.
