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It’s easy to get caught up in tourist traps and miss out on local gems when visiting a new place — especially in a big city like Chicago. Luckily, Airbnb makes it easy to feel at home in any city and Chi-Town is no exception, steeped in history, culture and home to some of the best pizza in the world. We found some of the best places to stay in the Windy City; whether you’re planning a relaxing staycation or visiting for the weekend with a group, check out these Airbnb rentals for an interesting stay that’ll fit most budgets and tastes.
Value Deals (less than $200 per night)
If you’re looking for an up-and-coming neighborhood that’s affordable and authentic but still includes lots of shopping and eateries, this is it. This charming two-bedroom apartment is perfect for travelers looking to explore the Bucktown and Wicker Park areas. Appropriately dubbed the fourth hippest neighborhood in the US by Forbes magazine, the area is known for its chef-driven restaurants, lively nightlife and countless art galleries. Rates from $148 per night, with a three-night minimum stay required.
Hello, gorgeous! Step into this two-bedroom penthouse conveniently location in Old Town, where travelers will be spoiled by the variety of restaurants and boutiques nearby. This sleek, modern unit is the perfect place to relax and unwind for a few days. Who wouldn’t want to wake up late in a king-size bed and take in that city skyline? If that’s not enough, there’s a rooftop deck that almost overshadows the spectacular indoor amenities. Rates from $175 per night, with a two-night minimum stay required.
Add this gorgeous two-bedroom Art Deco loft in Wicker Park to your Airbnb wish list — it’s cozy, artsy and big on residential style, while the décor complements the host’s creative side and features one-of-a-kind artwork from around the world in a space that sleeps up to seven. Rates from $179 per night with a two-night minimum stay required.
Mid-Tier ($200–$350 per night)
House all your friends and family in this gorgeous two-bedroom Gold Coast apartment, located just steps away from the Red (transit) Line. After a long day of exploring downtown Chicago, weary travelers may want to stay in and enjoy the indoor fireplace. Rates from $266 per night with a two-night minimum stay required.
This charming Bucktown loft is characterized as a Mad Men–styled three-bedroom apartment nestled above a store that sells absurdly soft shirts. While there’s not a full kitchen — just a kitchenette, despite the ample space — the apartment is situated near tons of great food and live music, and guests can get a sweet discount on clothing in the shop below it. Rates from $300 per night with a two-night minimum stay required.
High Roller ($350+ per night)
Located in a high-rise apartment complex, this renovated Gold Coast pad sits just two blocks from the famed Michigan Avenue. Situated on the 14th floor, this luxury two-bedroom, two-bathroom unit has an open living room and kitchen that’s great for entertaining. Complete with a hot tub, outdoor grill and pool, you can’t go wrong with choosing it over a pricey hotel room. Rates from $365 per night.
This brightly colored Gold Coast unit is the perfect apartment for a romantic getaway — or any kind of getaway for that matter. Travelers who appreciate minimal style will enjoy this cozy garden apartment where you can have the best of both worlds: the privacy and luxury of your own spacious suite, plus the amenities and services of a Chicago boutique property. Rates from $405 per night.
There’s five-star glamour at every inch of this commodious Wicker Park home, a luxury pad that’s ideal for a family or group of friends, with room for six to eight across five bedrooms, a chic dining area and a well-appointed kitchen. It also makes a great base for exploring one of Chicago’s most popular neighborhoods and the areas that surround it. Rates from $1,306 per night.
Maximize Your Purchase
There are plenty of ways to maximize your stay with points and miles. If you’ve never used Airbnb before, sign up through TPG to get $40 off your first booking — and the gravy train doesn’t stop there. Book through the Delta portal and earn 1 SkyMile for every dollar spent on your stay, and make sure to charge the purchase to a travel rewards card to rack up extra points. Using a card like the Chase Sapphire Preferred will get you 2x points on all travel purchases while the Chase Sapphire Reserve will get you 3x points on an Airbnb stay. When you combine the two, you’re effectively double-dipping with your points earning.
Prices are accurate as of publication date but are subject to change. All photos courtesy of Airbnb; featured image by Jeffrey Greenberg / Getty Images.
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