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Coin a buy ?
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What are you looking for ? Time of year ? Where are you staying ? What kind of food do you like ? You eating with the kids ?
General Advice:
Architecture River Cruise (Architecture Foundation is the best but $$)
Any of the Museums - Field Museum, Aquarium, Science and Industry are the best
So much amazing food get a Chicago style hot dog, Italian Beef Sandwich (dipped), Deep Dish Pizza from Gino’s, Donuts from either Doughnut Vault, Beacon or Do Rite, a steak from Gibson’s, Bavette’s or Swift and Sons, any of the Hogsalt Restaurants are 🔥🔥, Bazaar Meats (maybe leave the kids for this one). Skip the Bean. Walk the River Walk or the Lakefront
Stay in streeterville/ river north ish. Go to the children’s museum and navy pier. The zoo is amazing and free. You can also knock out the field museum and/or aquarium. Those were the best spots when my kids were very young and all within 10-15 min of those neighborhoods.
What kind of advice are you looking for? Your whole post seems to be about expenses, so are you just asking for cheap accommodations? I don’t really understand what help you need.
Well you have three adults for your three kids. That seems like an easy solve, each adult is responsible for one child. It won’t feel so daunting with so many little carpet munchers.
Maybe get an Airbnb otherwise the hotel situation may be odd two rooms with two kids for you and your wife then your MIL has one unless you have twins.
What would the kids do on a normal Friday during the day?
For all those little kids I’d look into an Airbnb vs hotel. Maybe here if you want to be close to downtown: https://stayinglevel.com/destinations/chicago/old-town/
Is this soon or what kind of weather are we talking about? You’ll definitely want to do the architecture boat tour on the river, Lincoln park zoo will be great if you have enough strollers, and if you can swing it a Cubs game is always a good time for the whole family.
You can take your wife and children to taste Chicago pizza first.