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How to Host & Entertain Guests for a Weekend Visit

I have a lot of weekends coming up where I'm hosting friends in town, and soon enough it will be summer, where guests seem to be in a constant flow in and out every single weekend (not that I don't love it - it is the perfect time to visit, and I love being able to show my friends why Chicago is my favorite city!)

It definitely requires a lot of planning and coordination, not to mention the costs can add up really fast. Taking friends to amazing restaurants and fun rooftops + activities is always a blast, but when you're playing host every weekend (when you'd normally be eating at home and cutting costs) it can take a major toll. 

I love playing hostess, and I think after two years of having guests in the city I've really started to master the ins and outs of making it work for everyone involved!


1. Clarify Logistics in Advance. Details such as when they plan to arrive, what time they plan on leaving, whether or not they'll have eaten upon arrival or before departing, whether they'll need parking or directions to your home are all the most useful if they're established well in advance. This will also spare you from any startling surprises (like a guest arriving before you're even home from work!)

2. Always Provide the Basics...& A Few Extras. Despite the fact that this is home to you, your guests are on vacation! You'd never want to stay somewhere on a trip that didn't have some basic essentials. I always aim to keep clean, fresh towels + linens, extra blankets, and travel size amenities like shampoo, conditioner, toothpaste, and spare toothbrushes on hand. I also make sure they know where to find everything so that they feel comfortable helping themselves (which in reality means less work for me, too!). Showing them how to use the coffee maker, find a glass of water and other beverages, the location of a hair dryer, and how to get the shower temperature to a reasonable level makes things much easier. Is it just me, or is it always difficult to find the right temperature in other people's showers?!

3. Use Your Local Knowledge. Obviously, people are going to want to explore the city and everything it has to offer (especially if they've never been!) This might mean that they're drawn to touristy and usually pricier spots. Expensive brunches, expensive tourist spots, and places farther out of the way that require pricier Ubers. It's great to show them what the city has to offer, but you know your city best! Keep a list of free and awesome activities on hand. For Chicago, I always recommend taking my friends to the Bean followed by a walk along the lakeshore to see the skyline and enjoy that amazing Chicago summer air. There are also options like renting bikes, exploring the parks, and checking out smaller local restaurants with better food and even better prices. 

4. Entertain at Home. You'll likely spend a lot of time out and about, but being the hostess that I am, I always think it's fun to plan a little dinner, some homemade waffles for brunch, or happy hour with drinks and appetizers when I have guests in town. There's something to be said for that little bit of extra effort, and it always leaves me with more fun memories than racing around the city and waiting in long lines that take us off of our schedule. If you're worried you won't have time to throw everything together, try making some appetizers or snacks in advance and refrigerating them! Then all you have to do is heat up, pour a glass of wine, and enjoy!

5. Have a List of City Favorites on Hand. Every once in a while, I run into situations where I have friends in town while I'm working or have other obligations and can't be available 24/7. In just a few weeks, I have two friends coming in town on a Wednesday night and they were looking for recommendations of what to do during the day while I was working! This inspired me to make a little guide of my favorite places for: where to eat, where to explore and walk around, fun evening activities for them to choose from (I'll be joining them, of course!), best photo-worthy spots, favorite coffee shops...this way, I won't feel guilty being unable to guide them, and they'll have plenty of things to choose from! I've already begun working on the list, and it's been so much fun to make!

Hosting friends for weekends is one of my favorite parts of being a Chicago resident in the summer (if for no other reason, it's a great time to prove to my friends why those winters are justtttt barely worth enduring). Following these tips has helped take the stress out of playing hostess, though, and lets my friend's vacations with me feel like a staycation for myself, too! 

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4 comments

  1. Love this list! I live in Charleston, SC and our home seems to need a front desk check-in with the amount of guests we have coming in and out, but we love it as well! The two most important things for me- having a nice wine and cheese spread when friends arrrive (like your photo) and a list of places to eat and have cocktails.

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  2. Some great advice!! I love it. Logistics is a critical (yet often over looked) detail.

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  3. We love entertaining and having people over to visit us! These are great reminders :)

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  4. I love taking my out of town guests to places they've never heard. They always enjoy the local places the best.

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