1.   Architecture Boat Tour

While its predominant demographic is tourists donning sunscreen and Nikons, this infamous tour is almost more gratifying for Chicago city-dwellers. It’s great for students who want a new perspective on appreciating the Windy City, and for those who haven’t spent much time outside of the Reg and need to get into the city over summer. It’s definitely pricey for something that is reminiscent of an educational experience, but more than worth the $40 plus tax. You don’t have to love architecture; just get into the spirit of curiosity and explore the city. Make sure you get on the top deck for the best views and most direct sunlight!

2.   City Lights Tour

If you’re hopping on the sightseeing tour bandwagon, or trolley, rather, the City Lights Tour is relatively cheap as downtown outings go. For $20, you’re taken on a whirlwind view of the city at night, alight. From Navy Pier to the Hancock Building, you can experience another, illuminated, view of the city. Jump on it now, because this tour is only offered until September.

3.   Broadway in Chicago

They say go big or go home, and when it comes to Broadway, the weeks of work are worth a night at the theater. This summer, Motown: The Musical will be showcased at the Oriental Theater as well as long awaited The Last Ship. The new The Last Ship, at the Bank Atlantic Center until mid-July, features an original score from Sting, inspired by his own childhood. Both are not to be missed. If your paycheck can’t quite cover the night out, or neither musical interests you, save the money for next season: Disney’s Newsies, Rodgers and Hammerstein’s Cinderella, and Book of Mormon will be here for winter.

4.   Chicago French Market

If food is more worth your dime, try the Chicago French Market. It’s like a vacation for your inner gourmet, which of course, we all have. Offering selections from numerous vendors of all ethnicities and cooking styles, you can purchase pre-made meals to eat in the market, bring fresh ingredients home to cook, or get something to go. Beware: While each vendor is fairly inexpensive, at this market, gourmands may find they have big eyes and even bigger appetites, so those loaves of French bread and tiny wheels of brie may start adding up. This market is definitely worth a fun outing, even if it’s just to walk around in the artisanal atmosphere and grab dinner or lunch to go.

(131 North Clinton Street, open from 7 a.m.–7:30 p.m. on weekdays and 8:30 a.m.–5:30 p.m. on Saturdays)

5.   Taste of Chicago

One of the most beloved festivals of the summer season, Taste of Chicago offers a sample of gourmet food, music stars, city history, and summer vibes. While admission is free, food events are not always gratis, and you’ll need tickets to see artists featured in the music shell. Artists this year include Janelle Monáe, Aloe Blacc, and AWOLNATION. There’ll also be pop-up restaurants, eateries that are open for only a day or two. Other vendors have booths, and some five-day restaurants will be open for the duration of the festival.

(Grant Park and along Columbus Street, June 9-13)