Thought I'd get this one started in the slow period. We may drive down there, which would be nice as far as having a car to get around. However, I hate the traffic in the Chicago area. Has anyone flown in and just used the train system? Looks like you could fly into O'Hare, take the blue line to the Loop Friday and stay in a hotel downtown a couple of nights. And on Saturday take the red line up to the purple line to the stadium and then back downtown after the game. It would be a lot of train riding, but it avoids driving hassles and parking hassles.
Chicago traffic can certainly be awful and unpredictable, but the game is in Evanston, not Chicago, and on the side of the metro area closer to Minnesota. If you can delay your arrival in Illinois to after 8PM Friday, or early Saturday you probably are not going to have a real traffic issue. The problem with this plan is that much of the appeal of attending a Gophers game at Northwestern is the opportunity to spend time in Chicago, not get stuck in Winnetka and then drive south to for the game only.
I prefer to drive to Milwaukee and head south on I94 to Chicago, and sometime I will divert from the tollway and drive on Illinois 45 that has some stoplights and goes through the old money suburbs along the lake north of Evanston. I find a lot of the traffic headaches associated with driving to Chicago center around I90 between Rockford and the Chicago city limits. I also find the number of toll booths to be awful on this stretch. This method adds about 18 miles to the trip, but Milwaukee traffic is light, and the drive less annoying.
It is possible to navigate around Chicago by car fairly easily once you are there, but the bigger problem is the incoming interstate traffic, especially if something like Lalapalooza is going on. Getting from the loop/ near north side to Evanston is fairly easy on Lakeshore Drive to Sheridan, or even on Clark Street.
For me the biggest challenge in driving to Chicago is finding free parking in the core city by my hotel after 5PM, or else getting stuck paying awful daily parking rates near the hotel. ($45-70 per night) For me visiting Chicago means I need to stay at a hotel on either side of the Chicago River, or north of the river, fairly near the lake/Michigan Ave/ State St. area. I will settle for the main loop/ Grant Park if I have to, but being right off Michigan Ave is the key. Being able to walk to the Oak Street Beach, or North Avenue Beach is also a plus. I probably need to fly to Midway and take the Orange Line to my hotel then take the RED/ Purple lines up to Evanston for the game.