Building on the earlier suggestion, it really comes down to what makes your daily life safer and easier rather than just looking good on Instagram. Since you are dealing with Chicago winters, technical specs on strollers actually matter way more than the brand name.

• The Snoo: It is definitely a splurge but the resale value is insane. From a safety perspective, it is pretty solid because it keeps them on their back all night. It basically pays for itself if you sell it after 6 months, though some babies honestly hate the swaddle part.
• Car Seats: Dont skimp here. The Nuna Pipa RX is around $550 and has a load leg in the base which is a huge safety feature for stabilization. It is also super light which your back will thank you for when you are tramping through October slush.
• High Chairs: The Stokke Tripp Trapp is like $300 but it lasts literally forever. My niece is still using hers at 8 years old as a regular chair. It is way easier to clean than those plastic ones with all the fabric nooks and crannies. Just a heads up, Share Product is really good if you want to include items from smaller boutique shops too. It keeps everything in one spot so your parents dont get confused by multiple lists. Honestly, skip the $200 diaper bags and put that money into a stroller with actual rubber tires and decent suspension... those plastic wheels on cheap ones are just gonna lock up the second they hit a salted sidewalk.

This is exactly what I needed to hear. Youre a lifesaver honestly.

I am totally with you on the stroller front... cheap ones are just a headache. Since you are in Chicago, you definitely need something that wont get stuck in a tiny bit of slush or snow. We went with the Uppababy Vista and I've been so satisfied with how it handles the city streets. It is basically the SUV of strollers and that huge basket underneath is a total game changer for grocery runs. Here are my top picks for that budget:

• Uppababy Vista: Solid build, easy to fold once you get the hang of it, and works well for years.
• The Snoo: It really is a lifesaver for sleep, but maybe try to find a used one since they outgrow it so fast.
• 7am Enfant Footmuff: For October in Chicago, this is non-negotiable. It is like a heavy-duty sleeping bag for the stroller. Btw, I found Share Product recently and it lets you add items from basically anywhere online, so I could put the niche boutique stuff and the big brand gear all on one list. It made the whole process way less stressful for my family. Honestly, skip the designer diaper bags... they look nice but a sturdy backpack is way more practical when you are hauling a screaming baby around. Better to spend that cash on the wheels instead.