Wrigley Field: As everyone knows Wrigley Field is much older than almost all of the other stadiums and it is more of a tourist attraction than sports stadium. Going to Wrigley to watch a baseball game is not like being at Busch Stadium or Miller Park. There are many insider tips which can make a visit to Wrigley more enjoyable. To start with the bleachers are completely separate from the rest of the stadium. They can only be entered by a separate entrance at the back and you have no access to the rest of the stadium. Promotional giveaways are not given to people in the bleachers and there are no beer vendors. It is open seating and if you want to sit near the field you will have to get there at least an hour early. There are only 3 other entrances to the stadium so it can be slow. The stadium club entrance is usually much faster, can be used by anyone and is on Addison. Leaving can take up to half an hour so consider moving near an exit towards the end of the game.
The food at Wrigley is pretty bad so either eat before or bring in a sandwich. A subway is a lot cheaper, better and healthier than anything they offer. The beer is mostly the usual Bud products, but a select few stands sell better beer. The best is the Dunkin Doughnuts by the front entrance. No one thinks they have beer so there is no line. The drawback is you only get 12oz instead of 16. Beer sales stop at the end of the 8th inning or at 9:00 pm whichever comes first. After that there will be no more beer at Wrigley. There is a nice deck on the upper deck above the main entrance. It is in the sun, so it can be a good place to warm up on a cool day, has beer and a nice city view.
St. Louis Cardinal and Milwaukee Brewers fans can feel a little safer at Wrigley Field now that there is inter league play. While Cub's fans still hate the Cardinals and Brewers it is the White Sox who now draw most of their wrath.
Weather is often an issue. It can be and usually is cold early in the season, even in May. I went to 7 straight opening days that were below 40 degrees. Wrigley is less than a mile from the lake so in Spring it can go from sunny and 60 to cloudy and 45 in a matter of minutes. If you are in the bleachers bring sunscreen because you will be in the sun for the whole game.
Transportation: Getting to and from Wrigley Field can be a difficult. Traffic can be a problem if you drive. Night games are especially bad because you have to fight the game traffic along with rush hour traffic. Parking is very expensive. Places near Wrigley Field can be up to $40, with easy out costing more. If you are willing to walk you can find $20 parking. Cars are often boxed in so if you want to leave early you may have to wait for someone else to show up. If you take more than an hour after the game to get your car they will have it towed.
Cabs have the traffic problem, but you avoid the parking issue. They can be hard to come by after the game, but if you walk a block or two from the stadium you can usual get one pretty quickly.
The best option is usually the train or El. The red line stops next to Wrigley Field and runs straight to downtown. It is $2.25 and avoids all traffic problems. It can be crowded after games and on the way to night games. One option is to take the much less crowded brown line and get off at Southport. There are several good taverns and restaurants on Southport, but it is about a 15 minute walk to the Cubs game.The number 145 and 146 buses run from N. Michigan Ave. to Addison and the lakefront, where it is about a 15 minute walk to the Cubs games.
Hotels: There are not really any good option to stay near Wrigley. There are no nearby attractions or sights. The best thing to do is to stay downtown and take public transportation to the game.
Tickets : A poor showing in 2013 has fans a bit apathetic and tickets will be a easier to get in 2014. It it worth checking with the box office right before the game because the Cubs do release the tickets they have saved for the players or other VIPs. If you are lucky you can get box seats. They also release seats on their website. I was able to get good seats for opening day weeks after the game sold out by checking back everyday until some became available. There are lots of legal scalpers, they must have a store front, and illegal scalpers. They have a lot of tickets and they will try to squeeze every dime they can out of you. Try to avoid using these people. Bleacher seats are always a hot ticket. Rooftops are rented as a whole so there are no individual tickets. Stubhub has a lot of good seats, often for below face value for most games.