Looking for a Bed and Breakfast in Logan Square? Try These

If you’re traveling and looking to truly experience the Logan Square neighborhood, consider booking a couple of nights at a bed and breakfast (B&B).

B&Bs provide a great accommodation option for anyone looking for a relaxing escape. They offer a cozy and personalized lodging experience that you can’t find at a hotel.

When staying at a B&B you can expect to receive a huge bang for your buck. Bed and breakfasts tend to go out of their way to make guests comfortable, by providing extra attention and service to make your trip feel special.

Additionally, bed and breakfasts make for a great way to truly live like a local. They provide visitors with a homey setting in the heart of the place they’re looking to explore.

Discover a few of the best bed and breakfast in the Logan Square area:

Longman and Eagle (2657 N Kedzie Ave)- This contemporary take on a traditional Chicago inn offers drinking, eating and sleeping options all within a comfy space. Each one of the six rooms provides casual accommodation for ‘urban travelers’ looking for an immersive experience within the heart of the Logan Square neighborhood.

Along with a tasty dining menu, Longman and Eagle also boasts an incredible whiskey selection.

Ray’s Bucktown Bed & Breakfast (2144 N Leavitt St)- If you’re looking for a charming place to stay, this is a great option. Located minutes from Logan Square neighborhood, Ray’s provides a true bed & breakfast experience. Guests can stay in one of the 11 unique rooms, complete with impressive amenities like free wifi, laundry facilities, computer access, a sauna, and a steam room.

Every morning you can expect cooked-to-order breakfast served whenever you would like. The menu is always complete with extensive, fresh ingredients.

Roscoe Village Guesthouse (2104 W Roscoe St)- This contemporary inn provides a unique and urban accommodation near Logan Square. While the guesthouse is within walking distance to plenty of restaurants and attractions, it is situated on a quiet neighborhood street to ensure a peaceful stay.

Each room is recently renovated, with all of the necessary amenities. This is an excellent option if you’re looking to travel with your family!

Wicker Park Inn (1331 N Wicker Park Ave)-  For high quality and hip boutique B&B, consider staying at the Wicker Park Inn. Not only is the space extremely aesthetically appealing, but it also provides easy access to the trendy Wicker Park neighborhood and Logan Square.

The bed and breakfast is situated within a historic Chicago home, fully renovated and decorated with intricate attention to detail and complete with modern amenities.

Guests can also choose from gourmet, mouth-watering breakfast choices daily.

Book your bed and breakfast in Logan Square and start preparing for a trip you won’t forget!

The Best of Logan Square Shopping

Logan Square continuously ranks as one of the coolest and hottest neighborhoods in America, and it’s easy to see why:

Along with incredible dining, nightlife, and housing options, Logan Square shopping has also put this trendy neighborhood on the map. In fact, a few years ago, Women’s Wear Daily named Logan Square as the next up-and-coming shopping destination in Chicago.

Shopping in Logan Square

Most of the Logan Square shops are sprinkled along or near Milwaukee Avenue and within walking distance of the famous ‘Square’.

The Logan Square neighborhood is a huge advocate for supporting locals. From breweries pouring local drafts to restaurants serving locally sourced bites, it’s evident that the community is all about supporting each other, and the shopping scene is no exception to this trend. Many of the Logan Square shopping features locally owned businesses and boutiques. The neighborhood also boasts an impressive selection of funky resale and vintage shops.

What to Expect

Strolling down the Milwaukee Avenue shopping district, you’ll quickly realize that Logan Square has perfected its charm. All along the street, you’ll find an assortment of quirky and attractive storefronts, complete with equally adorable interiors. Regardless of what you’re looking for, chances are you can find a Logan Square shop to meet your shopping needs. If you’re on the hunt for a brand new wardrobe, check out one of the multiple fashion-forward boutiques:  

FELT is the place to check out if you’re in need of a killer weekend outfit.  The owners are all about featuring emerging designers’ merchandise.

Tusk is another fashionable spot to spice up your wardrobe. Here you can find everything from chic outfits, to handcrafted jewelry.

For a fun gift shop, be sure to stop in Shop 1021 for handmade cards and curated gift boxes. Consider adding a stylish floral arrangement from Fleur Inc to your gift to make it extra special.

If you find yourself with a sweet tooth after a day of shopping, stop by Katherine Anne Confections or grab a fresh slice of pie from Bang Bang Pie Shop.

For some open-air shopping, don’t miss out on the Logan Square Farmers Market. The year-round market is located right along the neighborhood’s historic boulevard and remains a crowd favorite, offering fresh produce and endless entertainment.

Whether you’re considering making Logan Square your home, or you’re spending a day in the eclectic neighborhood, be sure to take advantage of the Logan Square shopping scene!

Things to Do on a Night Out in Logan Square Chicago

In recent years, Logan Square has transformed into one of Chicago’s most quirky and vibrant communities.

Along North Milwaukee Avenue, the neighborhood’s social hub, you can find plenty of funky restaurants, trendy cocktail bars, and craft beer taverns sprinkled along the street. 

Discover a few of the go-to spots to spend a night out in Logan Square, Chicago.

Best Spots for Nightlife in Logan Square

Once the sun goes down, the nightlife scene in Logan Square begins. 

Head over to East Room for a night full of dancing and DJ,. This stylish, cash-only bar offers a cool club vibe, with the crowd trickling in around midnight most evenings.

Slippery Slope is another favorite place for dancing the night away. While the main floor feels like an 80’s new wave dance club, the upstairs has the vibe of a 70’s cocktail lounge, complete with skee ball.

If you’re looking for a quirky late-night bar, check out The Owl. Here you can find over 20 rotating beers on draft, a 100-CD old-school jukebox, and doors open until 4 am. 

Best Spots for a Date in Logan Square

The Logan Square neighborhood is in no shortage of date night spots.

Spend an evening out with that special someone at Billy Sunday, an old-school inspired cocktail lounge. Sip on a mouth-watering, hand-crafted cocktail amidst the dark and charming interior.

Penumbra Wine Bar is another excellent choice if you are looking for a romantic setting. This Latin-inspired steakhouse and wine bar offers seafood dishes, cocktails, and beers complete with an intimate and charming ambiance.

Webster’s also has a reputation for romance and fine wine. Sit back, relax, and choose from an extensive list of global wines within this European-style wine bar.

Best Spots for Tourists in Logan Square

If you’re visiting Logan Square or expecting visitors, be sure to make an appearance at the favorite neighborhood bars.

Emporium has gained a reputation as one of Logan Square’s most innovative entertainment destinations. Here you can find an impressive selection of craft beer and games- from classic arcade games to pinball, foosball and air hockey. 

On a beautiful evening, Parson’s Chicken and Fish is the move. With one of the best patios and tastiest food in the neighborhood, this place won’t disappoint.

Recently named as the best cocktail bar in America, Lost Lake will surely impress. This funky tiki bar features incredible drinks within festive tropical digs.

With so many hot spots to choose from, it’s easy to spend an eventful night out in Logan Square!

Logan Square Chicago Restaurants That You Have to Try

Strolling the streets of Logan Square, you’ll quickly find that the dining scene is something the neighborhood takes very seriously. This hip community prides itself on offering an impressive selection of phenomenal eateries and delicious cuisine.

Discover a few of our favorite Logan Square, Chicago restaurants.

Top Restaurants in Logan Square

When it comes to Logan Square restaurants, there are plenty of neighborhood favorites sprinkled throughout the area

Longman & Eagle is a popular spot on any occasion. Whether you’re looking for a fun brunch or a tasty dinner, this farm-to-table restaurant serves fresh bites in a contemporary inn setting. You can even reserve one of their six rooms to stay overnight!

The farm-to-table trend is extremely popular in Logan Square and continues at Cellar Door Provisions. This rustic cafe and bakery will make your tastebuds melt with the tasty selection of homemade bread, flaky croissants, and out-of-this-world quiche.

Owen & Engine makes the perfect dining option on a cool night in the Windy City. The inviting English pub offers a creative twist on British fare, a rotating menu of tap and craft beers, and a cozy fireplace to enjoy.

Different Types of Food You Can Grab for all Occasions 

If your palette prefers variety, rest assured that Logan Square offers a wide selection of cuisine.

When you’re in the mood for Mexican fare, there are a couple of great local options to choose from. Both Mi Tocaya Antojería and Quiote have established fantastic reputations for their creative interpretations of traditional Mexican dishes and their beautiful interiors.

If you’re looking for jaw-dropping food creations and mouth-watering flavors, be sure to check out Fat Rice. This funky restaurant’s unique dishes are inspired by the flavors of Macau, a former Portuguese territory off China’s coast.

For a classic NYC pizzeria experience, stop into Paulie Gee’s. This rustic-chic eatery delivers a charming ambiance and Brooklyn’s most iconic pizza.

Best Spots for a Night Out, Date, or with Friends

If you’re looking for Logan Square restaurants with great atmospheres, you’re in luck.

For a cozy date night, consider bringing your special someone to Billy Sunday, a chic cocktail bar that provides upscale libations and gourmet gastropub. 

Daisies is another fun option for date night or a fun evening with friends. This stylish spot offers incredible pasta and an equally killer rooftop.

Take your dining experience up a notch at Masada, a hip Middle Eastern restaurant by day and flashy club by night. The expansive space features a tri-level patio, lounge, and room for DJs and performers in the evening. 

Whatever the occasion, Logan Square restaurants will not disappoint! Want to learn more about the Logan neighborhood? Check out our blog that covers more details about the history, bars, and available condo listings. 

Best Reasons to Live in Logan Square Neighborhood

Not only has this thriving neighborhood earned this coveted title due to its incredible walkability, beautiful historic homes, and trendy bars & restaurants, but Logan Square entertainment has also helped put this area on the map. Recently ranked as one of the “nation’s coolest neighborhoods,” Logan Square is earning an impressive reputation locally and nationally. We highlighted a few top reasons to visit or live in Logan Square.

History of Logan Square

Logan Square is one of the oldest neighborhoods in Chicago and possesses many historical monuments and buildings. Originally developed by early settlers like Martin Kimbell, of Kimball Avenue fame, in the 1830s the vicinity was annexed into the City of Chicago in 1889 and renamed Logan Square. 

Logan Square neighborhood is centered locally, on the public square that has been the neighborhood’s highlight at the intersection at Milwaukee Avenue, Logan Boulevard and Kedzie Boulevard. One of the defining characteristics of the neighborhood is the large grey-stone buildings and homes consisting of large bungalow-style houses.

Places to Visit in Logan Square

while the trendy neighborhood provides easy access to the ‘Loop’ and surrounding areas, you will quickly find that Logan Square has quite a distinct vibe of its own. This community is known for keeping things local. Throughout the neighborhood you will find local restaurants serving locally sourced food, local breweries pouring local drafts, local theatres premiering local artists, and local galleries showcasing local artwork.

If you are a fan of live music, catch a concert at Concord Music Hall, the newest addition to Logan Square’s and Chicago’s historic music scene. Also check out some of the neighborhood’s smaller venues, including Logan Square Auditorium where you will find various festivals and shows, or Rosa’s Lounge for some of the city’s finest jazz.

For fresh comedy and lots of laughs visit Logan Square Improv. Bring your own booze and enjoy stand up, sketch comedy, and improvised shows at this brand new comedy theatre.

On a rainy day, bundle up and enjoy a film at the historic Logan Theatre. Since 1915 this 906-seat movie house has provided a fun and affordable viewing experience, complete with sports vintage decor and a full bar and lounge. If you are a fan of independent films, be sure to attend the theatre’s Underground Film Festival taking place every June.

Do not miss out on the many art galleries Logan Square houses for the chance to admire unique creations and even partake in creating your own artwork.

Galerie F is a local favorite that showcases street art, gig poster, and collectibles from emerging local and national artists. The gallery also hosts monthly exhibitions and community drawing events.

Sideshow Gallery is also worth a visit. Here you can find an assortment of obscure and funky works of art, from vintage treasures to skulls and taxidermy.

Check the calendar at Comfort Station for upcoming art exhibitions, comedy shows, and other creative events. This calming, historic space opened its doors in 1926 as a warning station and has transformed into a local haven for all things artistic.

Logan Square Bars

If you are looking for an exciting spot to grab a drink, consider checking out one of the multiple arcade bars in the neighborhood. 

The infamous Logan Arcade offers the largest public collection of pinball and video games in Chicago, including 30 pinball machines and 47 video games. Plus, Monday evenings feature a movie night, and Tuesdays offer a magic show with a comedic twist. You can also enjoy a pop-up record shop on the last Wednesday of every month.

After major success in West Loop, Emporium recently opened its second location near Logan Square, bringing even more old-schooled games to the bar scene. Here you can find dozens of games, live music, DJs, and amazing local art murals. Be sure to hit the bar for curated craft beer and hand-crafted cocktails.

Alternatively, spend a laid night evening out at Cole’s Bar for a night of delicious drinks, pool tables, and live music. Also, check the schedule for the frequent and trendy comedy open mic nights.

After Cole’s, swing on by next door to Slippery Slope for another drink and a round of Skee Ball. You can also make your way to the dance floor and enjoy the live DJ.

Logan Square Restaurants

Check out Logan Square’s local sports club and eatery, Park And Field. The impressive outdoor patio features bocce courts, Adirondack chairs, multiple fire pits (where you can make s’mores), and a camper-turned-bar. The inside is decorated like an old-classic gymnasium, with things like vintage rings and pommel horses, so you may even feel like you’re working out while drinking at a bar. 

Lonesome Rose is a casual all-day spot is where you go to pretend you’re living in Southern California. The restaurant is light and airy with benches and large tables. It’s a great spot for large groups especially with the delicious Tex-Mex dishes on the menu that are easy to share. After you’re done, check out the downstairs basement bar, Golden Teardrops, for a change of scenery.

Middle Brow Bungalow is a cute brewpub that’s decorated with tea lights, reclaimed wooden picnic tables, and decorative plants. You must try anything made with the housemade bread or pizza. 

Mini Mott is the perfect spot if you’re looking for a very good burger. This casual corner spot tops their bugers with American cheese, frizzled sweet potato, and a hoisin mayo. The short menu here also has other items like a pork katsu sandwich, soft serve, and vegetarian jackfruit carnitas we really like.

The Moonlighter has an extensive menu of upscale bar food like waffle fries, nachos, and burgers. But the real reason to come here is for the huge outdoor space which features multiple fireplaces. Order a few pitchers of house cocktails, and it’s one of the best day-drinking spots in the city. Your furry friend is also welcome!

One of our favorite spots in Chicago is Fat Rice. The ambiance is low-key, and the Macanese food is outstanding. Stop into the colorful restaurant and try the bold flavors!

Condos in Logan Square 

Be the first to know about top Logan Square real estate in Chicago by working with Luxury Living Chicago Realty. We have access to the best Logan Square condos and are ready to help you discover your new home. View our current luxury Logan Square condo listings.


Our 7 Favorite Logan Square Boutiques

Local seems to be the trend in the Logan Square neighborhood. From breweries pouring local drafts to restaurants serving locally sourced bites, it is evident that the community is all about supporting each other; and the shopping scene is no exception to this trend.

Logan Square is known for its impressive assortment of local boutiques frequented by residents and visitors alike.

Discover the Luxury Living Team’s seven favorite Logan Square boutiques.


  1. Birdseye Rule: This charming boutique’s story is equally as adorable as the store’s collections. Two sisters living in the neighborhood decided to open the shop to honor and showcase their love for their Midwestern roots. The name was inspired by a family tradition established by their great-granddad’s at their little lake house in Michigan. Today the store carries an array of eclectic and hipster goods, including fun mugs, vases, and candles.
  2. Urban Rebel: Shernett Shaby opened this boutique following the success of her two other high-end stores in Toronto and River North. While the Logan Square shop still offers beautiful clothing, she describes this location as feeling more relaxed. Urban Rebel also doubles as an incubator for local artists, with local artists and poets performing frequently.
  3. FELT: If you are in need of a killer weekend outfit, pencil in a trip to FELT. This chic women’s fashion boutique delivers modern and trendy apparel from emerging designers. In 2015, Women’s Wear Daily named Logan Square as the next up-and-coming shopping destination in Chicago.
  4. Fleur Inc: Here you can find some of the most impressive floral arrangements in the city. This boutique floral shop adds a creative and stylish twist to every single flower bouquet. Additionally, you can find candles, cards, and baby items at the shop.
  5. Tusk: This contemporary bohemian boutique offers a bright and clean space to browse plenty of fun finds, all locally created. From funky clothing to handcrafted accessories, this is the one-stop shop to spice up your wardrobe. 
  6. Wolfbait & B-girls: With clothing and merchandise from over 250 Chicago designers and artisans, well as Chicago‐based fair‐trade companies, this boutique takes local to a whole new level. The boutique is female‐owned and operated by two native designers.
  7. Shop 1021: If you are looking for the perfect gift, this is the spot. This lifestyle and stationary boutique offers an impressive selection of handmade carts and an assortment of cute gift items. This boutique will even simplify your gift giving process with the Box of Shop- a perfectly curated “box” of gifts to celebrate any occasion.


Treat yourself to a shopping trip and check out these exciting Logan Square Boutiques!

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