Some Chicago hotels do offer shuttles or can help coordinate group transportation for your wedding weekend, but offerings vary by property. Many downtown hotels rely on the city’s easy transit options and rideshare availability, while others, especially those near airports or in the suburbs, may have shuttles already built into their services.

If transportation is important for your plans, it’s always helpful to ask early.

Once your block is set, most Chicago hotels will give you a customized booking link that guests can use to reserve their rooms online. Some properties also offer a dedicated phone number for guests who prefer to book directly with the front desk. You can share the link on your wedding website, invitations, or group emails whatever feels easiest.

Many Chicago hotels do require some form of deposit or contract, but it varies widely by property. Some offer “courtesy blocks” with no financial commitment, while others may ask for a small deposit or minimum pickup depending on your dates and how many rooms you need.

If your wedding falls during a popular weekend or downtown event, hotels may be a bit stricter with their policies. Still, Chicago has a wide range of options, so it’s usually easy to find something that fits your comfort level.

Yes! Chicago’s hotel rates can shift depending on the season. Summer and early fall tend to be the busiest (and often priciest) because the city is full of festivals, lakefront events, and visitors enjoying the warm weather. Big convention weekends can also affect pricing, no matter the time of year.

If your wedding is in winter or early spring, you may find more flexible rates and wider availability. No matter the season, exploring your options early usually gives you the best chance to secure a comfortable price range for your guests.

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It’s usually best to reserve your room block in Chicago about 6–9 months before your wedding. If you're planning a downtown celebration or expecting many out-of-town guests, locking in your block on the earlier side is even more helpful. Early booking gives your guests plenty of time to plan and makes the whole process feel smooth and stress-free.

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