Every year, tourists rush to Chicago because it’s a lovely city with a lot to offer.. But with so many wonderful possibilities, knowing where to start is difficult.

I’ve lived here for over 30 years, and I tell all of my visitors to utilize public transportation, explore the neighborhoods, and drink Malört at their peril.

Learn about the local sports culture, absurd taxation, and the ketchup rule. That’s just for starters. I’ve compiled a list of the best insider advice for a successful trip to Chicago.

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1. Plan a three to five-day visit

Seeing the highlights will take two to three days. These include the Art Institute, Wrigley Field, Millennium Park, and the Willis Tower. You can explore the neighborhoods, which are where Chicago’s real heart beats, and leave the city center by extending your trip by a few days. 

Pilsen and Logan Square greet you with chowhound cuisine and lively street art. Bronzeville features galleries and soul food eateries, while Andersonville is a jazzy, cafe-filled LGBTIQ+ hotspot. Hyde Park, Wicker Park, and Humboldt Park are also full of fantastic restaurants and attractions.

2. Do not drive particularly downtown

Driving in Chicago is not enjoyable. Snarls in traffic happen all day long, not just during rush hour . Road construction on the main highway through town has only exacerbated the problem. Furthermore, parking is scarce and expensive, especially downtown near the sites – garages regularly charge around $45 per day. To avoid the hassle, leave your car at home and take public transportation.

3. Purchase a Ventra Card for public transit

It’s easy to get around Chicago on public transportation, particularly the L trains. Both elevated and underground rails are used for its operation. They’ll get you to most attractions and communities till the wee hours. Buses fill in the gaps that the L fails to cover.

Invest in a rechargeable Ventra Card to use throughout transit and add value as needed to save time and money. Any L station, including airports, sells cards, which cost around $0.75 less per ride than single-use tickets.  Additionally, you can purchase a digital Ventra Card using the Ventra app. The app additionally offers bus and L timings.

4. Take the L to and from the airports

The aforementioned traffic is not a joke. Taxis and ride-sharing services can take forever to get from the downtown to the airport. Instead, take the L train. The Orange Line from Midway and the Blue Line from O’Hare both cost between $2.50 and $5 and take roughly 30 to 40 minutes. The L is not just faster than a cab, but it is also around ten times less expensive.

5. Reserve museum and theater tickets in advance

Many museums, like the Art Institute. Encourage visitors to purchase tickets online in advance through the museum’s website. A day or so before should suffice unless a major exhibit is going on.

Whether it’s for a world-class opera or drunken Shakespearean improv, it’s also a good idea to book theater tickets in advance. A week ahead is generally enough time. Browse Hot Tix for half-priced same-week drama, comedy, and performing arts tickets – an ideal gift for budget-conscious travelers.

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