Flight
There are two main airports in Chicago: O'Hare and Midway. Midway is the main airport for Southwest flyers (my preferred airline) and O'Hare is likely the hub for any other airline. Sal (see travel "note") can pick you up at either airport, and will text you with details on where to meet him when you arrive. Cabs are abundant at both airports as well. Midway is a tad closer to downtown Chicago, but there's not a huge difference, quite honestly. O'Hare's has a Garrett's popcorn which is the absolute best caramel corn you'll ever have. If you happen upon it, make sure to order the "Chicago Mix".
Travel Note
I'd highly recommend using Sal for any transportation to and from the airport. He's a limo (black SUV, basically) service that I use for all of my business transportation needs. He is ALWAYS on time, extremely communicative the day of, and is a safe, friendly driver. His negotiated rate for our wedding is $60 one way, which is slightly more expensive than taking a cab or Lyft, but 100% worth it in my opinion. If you'd like to use Sal, please coordinate with me directly by email or text: kristingene@gmail.com or 209-918-4777.
Train
Chicago's public transportation system is very robust, and pretty easy to navigate. If you feel like taking the train from the airport into the city, you can...but there's no super easy direct route to get from either airport to the Four Seasons (if that's where you stay). Google Maps is a fantastic resource to help you navigate the trains, and any hotel you stay at should have Chicago Transportation Authority (CTA) info - train and bus. I'd recommend the train or bus to get around the city, especially up and down Michigan Ave., if you decide to do any shopping. There are buses that constantly run down Michigan and stop practically every block. The fair is $2.25 (exact change only).
Hotel
This is where we will be hosting our Wedding Ceremony + Reception. When making your reservation, make sure you tell them it's for Lou and Kristin's wedding, and they will give you our negotiated rates, which are: King Suite: $245 (+ tax) Executive Suite: $345 (+tax) One Bedroom: $675 (+tax) We love the Four Seasons, and hope you'll join us there!
Hotel
We're also a huge fan of any of the Kimpton hotels in Chicago, and there are four. I don't have a preference, but the Gray is one of their newest. All Kimptons are known for their friendly customer service, award-winning restaurants, and a furry friend or two (they are pet friendly!) Also, I hear they're a phenomenal employer (right, Ali? ;) Other Kimptons in Chicago include the Allegro, the Palomar and Monaco. Prices range from $130 - $200 per night, and all are a short cab ride from the Four Seasons.