Chicago, the Second City, is a wonderful place filled with limitless possibilities--and also a million chances to blow your budget. But there are many things you can do in Chicago that will allow you to have fun while keeping your finances in check.
While many people find it useful to have a car in the city, you don't really need it. Chicago Transit Authority's (CTA) "El" is an easy and convenient elevated train line that takes you to most places in the city. The bus lines are also convenient and run frequently. To save on transportation costs, consider investing in a Chicago Plus Card. The electronic card allows you to maintain your traveling costs online--and even offers a monthly pay option. You pay $5 to activate the card, but for just $75 a month, you can get unlimited transport on all of the CTA's public transportation. It may seem steep up front, but when you add up the overall cost of transportation in Chicago, you're actually saving quite a bit.
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When looking for apartments, it's easy to be drawn to the downtown area. The thrill of living in a high-rise building can be tempting, but there are plenty of fun neighborhoods just outside the downtown city limits. Consider a neighborhood like Wrigleyville or Lincoln Park; both can still be little costly, but with some searching, you can find affordable housing. Uptown is a developing area with some surprisingly nice places to live. Consider some of the neighborhoods to the west of the city. If you absolutely can't afford to live within the Chicago city limits, there are plenty of suburbs that offer quick access to the city through a convenient Metra system. Be sure to check Craigslist for apartments and cheap furniture.
While the museums in the area aren't free, there are still plenty of fun options that expose you to culture. Millennium Park hosts a free summer concert series. And the amphitheater there is modern and very cool-looking--you'll be sure to have a good time. The city also offers seasonal festivals that are cheap and entertaining. The Taste of Chicago is a summer festival that features food from across the city, as well as entertainment. With careful planning, it can be a fun trip. Check out Daley Plaza during the holidays (Halloween, Christmas, etc.) for seasonal festivals. Also consider Looptopia, an all-night event in Chicago's "Loop," which features lots of free entertainment.
Chicago loves its sports, but ticket costs can be extreme. The good thing about the city is that there's a multitude of bars located near the stadiums and fields that cater to fans. Consider venturing to Wrigleyville if you're a Cubs fan and hitting one of the many bars along Clark Street. Many offer specials on game days.
If you want to get away for a weekend, consider booking a trip through Amtrak. Union Station serves as a bustling hub for tourists. If you plan early enough, you can get cheap tickets to many places in the country.
If you want to save money but still have fun on the weekend, consider heading to the beach of Lake Michigan. Catch some rays, play some volleyball and watch as boats float by. It's the perfect way to spend a day in the summer--and it's free!