Apartment holiday rentals in Wrigleyville, Chicago

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Top-rated apartment rentals in Wrigleyville, Chicago

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Guest favourite

Apartment in Lincoln Square

4.94 out of 5 average rating, 191 reviews

Spacious, light-drenched studio-private entrance!

Sun-filled private apartment in Lincoln Square! Spacious & well-appointed studio apartment features newly renovated kitchen and 1.5 baths (spa shower!) Located in the Lincoln Square neighborhood, you’ll be steps to restaurants, cafes, pubs & shopping. Close to CTA Brown Line (Rockwell) stop, as well as Western, Foster & Lawrence buses. Just 3.4 miles to Wrigley Field. One block to Swedish Covenant Hospital. Short bus/ride-share to Andersonville, Chicago Lakefront & Foster Beach! Kid friendly.

5 – 12 July

$1,542 AUD total

Superhost

Apartment in Roscoe Village

4.9 out of 5 average rating, 373 reviews

Relax and Enjoy Chicago in an Updated and Private Apartment in Roscoe Village

We converted our garden unit into a great space for travelers, we updated everything with you in mind, features high end appliances, full kitchen, 1 king and 1 queen pullout, heated floors, and free wifi. There are only 2 beds. We also have a landscaped backyard and grill access if requested If you need anything please let me know ahead of time Roscoe Village is often thought of as a small town inside the big city. It is one mile west of Wrigley Field and two miles west of the lakefront.

22 – 29 Oct

$2,360 AUD total

Guest favourite

Apartment in Lake View

4.97 out of 5 average rating, 244 reviews

The Garden on Wayne

Located in one of the top 3 neighborhoods in Chicago, a great spot for a couple, a small family, business travel or a weekend with the girls. Close to high end shopping, a world famous and historic theatre and dozens of restaurants, our quaint garden apartment offers a quiet spot in a great area for weekending - and is also the midpoint between O'Hare and Downtown. The Lakefront is a quick 20-minute walk; the Lincoln Park Zoo is 20 minutes in an Uber. Please see below for further detail

26 Mar – 2 Apr

$2,375 AUD total

Guest favourite

Apartment in Roscoe Village

4.96 out of 5 average rating, 238 reviews

Roscoe Village One Bed Lux Apartment Near Wrigley

5 Star Reviews! 1 Bedroom Apartment,King Bed, queen sofasleeper, OwnOcc. Bldg. Featuring Central Air, Private Balcony, Deluxe Kitchen Stainless Steel Appliances, Microwave, & More. 55" TV, Direct TV.This outstanding Location is steps from the Roscoe Village Business District and a quick walk to the Train Stop & Bus stops, to Downtown Chicago & United Center(Hawks & Bulls).Walk to Bars, Restaurants & Shops.All stays over 30 days will require Guests to Complete additional "Lease".,

15 – 22 Oct

$1,488 AUD total

Guest favourite

Apartment in Lake View

4.86 out of 5 average rating, 202 reviews

Private Queen Bedroom and En Suite Bath

Visiting Chicago? Stay in true Windy City style by joining us in our historic 3-flat in the Lakeview neighborhood on Chicago's North Side within walking distance of Wrigley Field and the popular Southport Corridor of restaurants, bars and shops. We love hosting and can help you tailor an exploration of our city that is perfect for your interests or occasion. Walking access to the Red and Brown Elevated lines and buses at the end of the block can get you throughout Chicagoland.

12 – 19 July

$1,769 AUD total

Guest favourite

Apartment in Lake View

4.97 out of 5 average rating, 329 reviews

Charming, Spacious 3BR Lakeview Apt Near Transit

This newly remodeled 3-bedroom unit with 1-bath apartment is perfect for both leisure & business travelers. Located on a safe, tree-lined street, in the Lakeview neighborhood, with a completely private entrance of it's own. We are just a 5 minute walk away from the CTA Irving Park Brown Line, which will get you downtown in less than 20min. We are also conveniently close to Wrigley Field, Lake Michigan, Bus Stops, and other great neighborhood shops, restaurants, and nightlife.

2 – 9 Jan

$1,866 AUD total

Guest favourite

Apartment in Wrigleyville

4.99 out of 5 average rating, 140 reviews

Modern vintage chic steps from Wrigley Field!

Vintage touches and modern updates in the heart of Wrigleyville! Close enough to see Wrigley Field from the building, yet the block is charming and quiet. Close to the lake and close to Boystown. The apartment's vintage DNA is beautifully respected while being updated with the modern amenities you expect when traveling. You will love the exposed brick and original millwork while enjoying huge new windows, an open floor plan, chef's kitchen, stylish decor and spa like bathroom.

4 – 11 Jan

$3,250 AUD total

Guest favourite

Apartment in Wrigleyville

4.94 out of 5 average rating, 105 reviews

The Crash Pad 1 min walk to Wrigley Field

Cozy Garden apartment a 1/2 a block from Wrigley Field and less than a 5-minute walk to the center of Wrigleyville where you will find dozens of shops, restaurants and Bars. Even though the apartment is close to all the action, this location is on a quiet street. Great spot to relax if you’re in town for a Cubs game or concert! 15 min walk to the lake and beaches. 15 minutes from downtown 5 min walk to 2 Rapid transit stations connecting you the rest of the city.

16 – 23 Oct

$2,637 AUD total

Guest favourite

Apartment in Lake View

4.99 out of 5 average rating, 230 reviews

A Whimsical Fairy-tale Loft in Ravenswood Chicago

Welcome to Bluebird Inn, an intimate, thoughtfully designed urban inn that will serve as an oasis as you embark on your exploration of Chicago. Nestled above the Long Room, a beloved neighborhood tavern and coffee house (Bad Johnny's, Nice Guy Food Co. and AJ's Bakery & Diner), you can start your day downstairs with breakfast and coffee and stop in for a nitecap before heading up to retire for the evening. Settle in & enjoy the amenities and approachable luxury.

31 Jan – 7 Feb

$1,960 AUD total

Guest favourite

Apartment in Uptown

4.96 out of 5 average rating, 267 reviews

Cozy loft in Chicago's Uptown

Located in the heart of Uptown, we offer a private, 3rd floor/walk-up, smoke-free studio apartment in a vintage Queen Anne (hosts live on 1st floor; apartment on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. Andersonville (one of Chicago’s coolest neighborhood is a 15-minute stroll. CTA's Red Line/Wilson train station is 3 blocks away. Overnight street-parking decals also available for guests.

16 – 23 Oct

$1,462 AUD total

Guest favourite

Apartment in Wrigleyville

4.8 out of 5 average rating, 385 reviews

'Secret Garden' Apartment in Wrigleyville

Small garden unit in the heart of Wrigleyville. Steps from both Wrigley and Boystown. The apartment has a queen bed in the bedroom and a sitting area with a TV and mini-dining area. In addition, the apartment has mini fridge, microwave, coffee machine w/ pods, and small dining table. There is no kitchen; fortunately Chicago has a multitude of amazing restaurants to choose from! Includes full bathroom with shower and linens.

20 – 27 Aug

$2,180 AUD total

Guest favourite

Apartment in Lincoln Square

4.96 out of 5 average rating, 323 reviews

Bright family-friendly Lincoln Square 2-bed 1-bath

Light-filled, comfy 2-bed 1-bath apartment on a quiet, tree-lined street in Lincoln Square on Chicago's north side. Spacious kitchen stocked with essentials, washer/dryer, and your own private porch. Walk to cute local shops, cafes, grocery stores and the Rockwell brown line stop. Pet and kid-friendly (in one of the city's most family-friendly areas). Street parking is free, easy and doesn't require a permit.

18 – 25 Dec

$1,770 AUD total