Not all adventures have to be in the wilderness. With one of the biggest metropolitan areas in the world being a short drive from town, it only makes sense to go explore it. Chicago has its share of opportunities for experiences you can have nowhere else. Try an ethnic food that you’ve never had. Gaze on some of the most revered artwork in the world. Stand atop one of the tallest man-made structures. Plan out a sweet buildering route. I’ve just barely scratched the surface of the city and I will admit that this guide is not particularly good. But it can at least be a starting place for planning an urban adventure.
The Field Museum (http://fieldmuseum.org/) will inspire you to set off on an epic adventure. It is full of interesting exhibits showcasing the many amazing wonders of the world. Other good ones include the Shedd Aquarium (www.sheddaquarium.org), and the Art Institute (http://www.artic.edu/).
The big city can get expensive real fast. And you need to ration your funds for more adventures, so hitting up the free attractions is always a good idea. The Lincoln Park Zoo (http://www.lpzoo.org/) is the best free zoo I’ve been to and is a great escape from the urban landscape. Nearby is the Conservatory (http://www.chicagoparkdistrict.com/parks/lincoln-park-conservatory/) where you can see some amazing plants from all over. Finally, be sure to stroll around Millenium Park and the lake shore. While the Sears tower charges a large amount to go to the top floor, the John Hancock building is pretty tall and you can get to the top for free. They will ask you to buy food or a drink to be up there, but you can just go to the bar, spend ten minutes pretending to look at the menu while taking in the view, then take off.
Garfield Park Conservatory – Totally Free and very warm in the winter
This thing is weird. If anyone finds a way to rappel off of it, let me know.
You aren’t going to want to drive into Chicago if you don’t have to. Getting there eats up a lot of gas, uses toll roads, and parking in the city is difficult and expensive. Try these other options.
South Shore train (http://www.nictd.com/) – This isprobably the best option for trips out of South Bend. The fare is $11.75 each way and it leaves and comes back multiple times per day. It leaves from South Bend Regional Airport.
Megabus (http://us.megabus.com/) – It is unfortunate that the Megabus line to South Bend only lasted a few short months. But if you are coming from a different city, check to see if they have routes there. If you book early enough it’s only $1 each way (not kidding).
Once you’re in Chicago, expect to do lots of walking. It’s really the best way to take it all in. You can also rent a bike (http://www.bikechicago.com/) if you want to be more efficient but still get places under yourown power.
Avoid hotels at all costs. They are super expensive and not the best way to experience things. Couchsurfing (www.couchsurfing.org) is the best option. It is completely free and you always get to meet some really interesting and friendly people that will likely be able to direct you to more cool places. But there is a high demand for couchsurfing hosts in the city. You should ask multiple people and you should start asking several weeks before the trip.
Another option that I haven’t tried but is probably useful is airbnb (www.airbnb.com), similar to couchsurfing but requires you to pay the hosts (usually much less than a hotel though).