16 Places That Will Make You Fall Back In Love With Chicago

Garfield Park Conservatory | © Peterson.jon/WikiCommons
Garfield Park Conservatory | © Peterson.jon/WikiCommons
On rare occasions, Chicago can be a city difficult to love. Between the harsh winters, frequent political turmoil, and a rampant barrage of potholes, it certainly has its off days. But during the hard times, it’s important to remember why you fell in love with the city in the first place, so revisit those reasons or maybe find a new one to help it happen all over again.

Oz Park
The Tin Man statue greets visitors at the corner of Webster and Lincoln Avenues at the entrance of Oz Park in Chicago's Lincoln Park neighborhood

Oz Park pays homage to characters from L Frank Baum’s ‘The Wizard of Oz’ | © D Guest Smith / Alamy Stock Photo

Oz Park is a beloved community green space in the Lincoln Park neighborhood, complete with a stunning wooden playground honoring L. Frank Baum’s The Wizard of Oz.

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The Original Rainbow Cone

Beverly’s Rainbow Cone on the far South Side has been a Chicago mainstay for 90 years. A seasonal operation, they serve rainbow-colored cones of ice cream, with orange sherbet, pistachio, Palmer House, strawberry, and chocolate flavors.

The Original Rainbow Cone, 9233 S Western Ave, Chicago, IL, USA, +1 773 238 7075

Rainbow Cone at The Taste of Chicago, courtesy of Flickr:

Rainbow Cone at The Taste of Chicago | © julie corsi/Flickr

THE original Rainbow Cone

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Mojo Spa

Pamper yourself at this chic Wicker Park spa. Mojo Spa is a full-service nail salon and sells more than 200 types of house-made beauty and cosmetics products.

Mojo Spa, 1468 N Milwaukee Ave, Chicago, IL, USA, +1 773 235 6656

Mojo jojo but less evil green monkey and more spa

A photo posted by Kelsey Laabs (@kelslaabs) on

h Street Books

Join the thousands of others who have gotten lost in this unassuming book basement hideaway. While Hyde Park’s 57th Street Books independently serves the local University of Chicago community, it is an attractive draw citywide.

57th Street Books, courtesy of WikiCommons

57th Street Books | © Mr. Granger/WikiCommons

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Pops for Champagne
Bar, Nightclub, Contemporary, $$$$

Pops for Champagne in River North offers 250 different champagne varieties, a full bar, small plates, live jazz music, and an unrivaled nightclub setting.

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Sun - Fri:
3:00 pm - 2:00 am
1:00 pm - 2:00 am

Garfield Park Conservatory
Garfield Park Conservatory

The Garfield Park Conservatory a perfect, quick and easy getaway for Chicagoans. | © Peterson.jon / WikiCommons

This two-acre greenhouse displays thousands of plant species for the public’s viewing pleasure. Visit the Garfield Park Conservatory year-round for your escape to nature.

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Thu - Tue:
9:00 am - 5:00 pm
9:00 am - 8:00 pm

Accessibility & Audience:

Accessible (Wheelchair), Kid Friendly, Family Friendly

The Palmer House

The historic Palmer House Hilton Hotel is as Chicago as it gets. Come for a luxurious stay in one of their suites or just enjoy the decadence and a drink in the main lobby.

The Palmer House, 17 E Monroe St, Chicago, IL, USA, +1 312 726 7500

The Palmer House, courtesy of Flickr

The Palmer House | © Sandra Cohen-Rose/Flickr

Pequod’s Pizza

Pequod’s has been one of the best pizzerias to fly under the mainstream radar in Chicago for decades. They’re most beloved for their thick, cheese-laden pan pizzas.

Pequod’s Pizza, 2207 N Clybourn Ave, Chicago, IL, USA, +1 773 327 1512

The 606
Hiking Trail, Park
The 606

Cyclists, runners and walkers on Chicago's gorgeous trail, The 606. | © Colin Hinkle / Courtesy of The Trust for Public Land

The City of Chicago recently transformed the old elevated Bloomingdale train tracks into a much-needed green space. Bike, walk or jog the nearly three-mile layout of the 606’s Bloomingdale Trail through Wicker Park and Logan Square.

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Sun - Sat:
6:00 am - 11:00 pm

Accessibility & Audience:

Accessible (Wheelchair), Dog Friendly, Kid Friendly, Family Friendly


Outdoors, Scenic

Room 13

At the Old Chicago Inn, you’ll find their hidden Room 13 Speakeasy. Just head down the side alley to be transported back in time with jazz music and themed cocktails.

Room 13, 3222 N Sheffield Ave, Chicago, IL, USA, +1 773 472 2278

Room 13 #speakeasy

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Mario’s Italian Lemonade

This seasonal spot for sweet treats has been delighting Chicago since 1954. Mario’s Italian Lemonade is a fixture on Little Italy’s infamous Taylor Street and caters to customers of every age.

Mario’s Italian Lemonade, 1066 W Taylor St, Chicago, IL, USA

This place. #EEEEEATS #infatuationchi 📸 @nataleegarza

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Myopic Books

Myopic Books in Wicker Park consistently ranks high in popularity among Chicago’s best bookshops. They have more than 70,000 books spread across three floors, plus they host poetry readings, author appearances, and occasional live music.

Myopic Books, 564 N Milwaukee Ave, Chicago, IL, USA, +1 773 862 4882

Myopic Books, courtesy of Flickr:

Myopic Books | © Lauren Manning/Flickr


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Streeter’s Tavern

In the ritzy area of upscale River North, Streeter’s underground, wood-paneled bar filled with games, beer, and good music is like a breath of fresh air. Come here for beer pong, pool, foosball, giant Jenga, cheap drinks, and all-night fun.

Streeter’s Tavern, 50 E Chicago Ave, Chicago, IL, USA, +1 312 944 5206

Nothing quite like winning beer pong with the queen boss @queenkrimins #coolestbossever #lovemyjob #queenofbeerpong

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The Waterfront Cafe
Cafe, Coffee, Tea , Vegetarian, American, $$$

Get away from the bustle of the city by recharging at Lake Michigan on the far North Side. The Waterfront Cafe offers unparalleled lake views and top-quality eats.

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Holy Name Cathedral
Cathedral, Church
Holy Name Cathedral

Holy Name Cathedral | © Nheyob/WikiCommons

Religious or not, Holy Name Cathedral is a stunning part of Chicago’s historic architecture. The breathtaking interior and rich history are more than enough reason to warrant a visit.

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It may be a big tourist draw, but Eataly is worth it. This massive food mecca sells and serves fresh Italian cuisine and numerous kitchen goods.

Eataly, The Shops at North Bridge, 43 E Ohio St, Chicago, IL, USA, +1 312 521 8700