The Good: 

A good combo of city and suburb feel, great value, easily accessible from nearly any city, and lots to offer during the day and night.

The Bad: 

The weather is not ideal for at least six months of the year and with no skiing close by, Chi-town has some limitations.

Vote Up/Down:
Vote Up/Down

B10 Overall Rating: 8. Surprisingly great bachelor party locale given the lower prices, easy access, friendly, and daytime activities during the warmer months.

Hotels: 8. You’ve got some of the nicest hotels and still at a great value.

Restaurants: 7. Very good, reasonably priced meals (yummmm, deep dish...).

Bars: 7. Tons of bars, especially cheap liquor, but the talent can lag in certain areas.

Clubs: 8. Nice clubs, lots of hotties, low $.

Gentlemen’s Clubs: 7.  Attractive girls, midwestern values...

Daytime Activities: 9.  Five pro sports teams, race track, beach, great drinking fests.

Price: $$



Chicago might be the most underrated city for a bachelor party. It’s one of the more balanced cities and almost has it all… at least from May-September. During the warmer months, the Windy City offers some of the best daytime activities from Cubs day games to Lollapalooza and the rest of the summer festivals, as well as a fun nightlife, fantastic food (especially for hangovers and recovery - hard to beat the pizza if you prefer deep dish), easy transportation (cabs are cheap plus there’s an easy rail system), friendly people (including the gals), and reasonable prices. 

The coasts and Vegas aren’t always the answer, so check out this Midwestern gem for your next guy trip.

For more details on this great city by category (eg, hotels, bars), see summaries in the quick fix box to the right and then check out our fuller Bachelor10 lists HERE.

Bachelor10 Tip: 

Chicago offers some of the best festivals throughout the summer so look into Lollapalooza, Sheffield Garden Walk, and combine with a Cubs game in the bleachers or on one of the rooftops.