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Chicago is one of the top getaways in the Midwest United States. This beautiful city sits on Lake Michigan, and it’s home to incredible museums, sports teams, restaurants, and outdoor activities. So I’ve rounded up the best luxury Airbnbs in Chicago.
The Best Airbnbs in the Midwest U.S.
From boutique lofts to spacious townhomes to high-rise apartments, these Airbnbs will let you explore Chicago like a local.
Here are the coolest luxury Airbnbs in Chicago!
Modern Retreat
4 guests bedroom2 beds bath
You’ll love the views and glass walls in this modern high-rise apartment. Industrial architecture is combined with warm colors and plush furniture to create an inviting retreat above the city. This apartment’s location on South Wabash in the South Loop also means you’ll be close to everything the city has to offer.
Urban Oasis
10 guests bedrooms beds3.5 baths
This iconic Chicago rowhome has room for your whole crew. You’ll have large living and diving areas, open-concept living, a large yard, and a beautiful deck that you’ll never want to leave.
Factory Conversion Loft
Factory Conversion Loft
2 guests1 bedroom1 bed2 baths
Welcome to your urban oasis! Prepare meals in a spectacular professional-grade kitchen. Relax in a one-of-a-kind former warehouse in one of Chicago’s trendiest neighborhoods. Then end your day in the Japanese soaking tub.
Rooftop Pool
4 guests bedroom beds1 bath
You’ll have the city at your feet in this stunning skyscraper apartment. This unit has access to the building’s rooftop pool, gym, and rooftop patios with grills. Plus, you’ll be able to walk to some of the city’s best restaurants and sites.
Budget Loft
4 guests · 2 bedrooms · 2 beds · 1.5 baths
If you want budget accommodation that still gives you lots of room, then this top-floor apartment is for you. You’ll have great views and a deck, and you’ll be just a short walk from restaurants, the metro, and shops. Plus, your furry friends can stay with you here!
Penthouse
6 guests2 bedrooms beds1 bath
Towering above the city, this two-story penthouse is the epitome of city living. You’ll love the massive fireplace, 20-foot floor-to-ceiling windows, and being close to the elegance and glamour of North Michigan Avenue and the artsy sophistication of the River North District.
Across From Wrigley Field
7 guests bedrooms beds bath
If you want to see a Cubs game, you can’t get any closer to Wrigley Stadium than this home. You’ll love the outdoor patio with a grill, yard, and outdoor seating. You might even catch a fly ball in your own front yard!
Luxury Highrise
8 guests bedrooms3 beds baths
If you want to feel like you’re in a luxury hotel, then this apartment is for you. There are direct views of Navy Pier from almost every window, and you’re centrally located for all of the city’s best attractions. You’ll also have access to the building’s state-of-the-art gym, heated indoor pool, sundeck, fire pits, grilling stations, and private cabanas.
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What are your favorite luxury Airbnbs in Chicago? Tell me in the comments below!
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Luxury Airbnbs in Chicago
Frequently Asked Questions
Is Chicago safe for tourists?
I felt very safe every time I’ve visited Chicago. But, as with any destination, you need to take precautions to keep yourself safe. Don’t walk by yourself at night, stay in a secure and well-located hotel or vacation home, use slash-proof, lockable, and RFID-protected bags and purses, and always have a charged cell phone with you.
What is the best month to visit Chicago?
June – August is Chicago’s peak tourism and festival season. Accommodation rates and crowds will be at their highest, so book hotels, Airbnbs, tickets, and tours in advance. These months are peak baseball season, so make sure you check if there are home games when you plan to visit. Home games will make prices and tourist numbers even higher. Average summer temperatures range from the high 50s to the mid-80s, so pack a mix of clothes and be prepared for rain in August.
September and October are beautiful months to visit the city. The foliage will be changing, and the temperatures will be pleasantly cool (you’ll want layers for the mornings and evenings). Accommodation prices and crowds will be on the decline, and the city hosts an incredible Oktoberfest.
Winter is cold and windy with high snow chances, and winter lasts from November well into March (daytime highs are in the low 30s to high 40s, but wind chills can cause temperatures to drop into the negatives). If you’re okay with the cold, then you can score some great hotel deals in these months.
Spring is short and beautiful in Chicago. April and May have daytime temperatures between the high 50s and low 70s, and the city is covered in flowers. Make sure you have rain gear with you during these months. Prices and crowds will be on the rise, especially around Spring Break weeks, but you can still find some great accommodation and airfare deals.
How do tourists get around Chicago?
It’s easy (and very enjoyable!) to walk around Chicago’s neighborhoods. But if you’re going to traverse the town, then you’ll want to use rideshares or the city’s metro lines.
Is Chicago an expensive city?
Chicago is a relatively expensive city to visit, but there are lots of free activities here. To save some money, visit on weekdays and during the shoulder of off-seasons, and eat out for lunch or prep your own meals.
How much is an Uber from O'Hare to downtown Chicago?
Because of Uber’s surge pricing, rideshares from the airport to downtown can range from $35-140 depending on the time of day. Pre-arranged taxis or shuttles can save you money and time when going from the airport to downtown. You can also take CTA trains (Chicago’s public transportation) to downtown for cheap.
Is it easy to drive in Chicago?
Not for visitors. Chicago’s packed streets, ever-changing road rules from hour to hour and day to day, stressful rules-of-the-road, and limited and expensive parking mean visitors should drive as little as possible while visiting Chicago (unless it’s to take a day trip).
How many days do you need to spend in Chicago?
Give yourself at least 4-5 days to spend in Chicago. This will give you plenty of time to explore some of the neighborhoods, enjoy the food scene, catch a game, see a show, and take a day trip.
Does Chicago have a beach?
Yes! Chicago’s 26 miles of scenic lakefront includes several public parks and gardens, an 18-mile Lakefront Trail, and more than two dozen free beaches. All Chicago beaches are open for the summer season from late May to early September.
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This article about the best luxury Airbnbs in Chicago is not a sponsored post, and the thoughts and opinions expressed in this post are entirely my own. Some of the links in this post about the best luxury Airbnbs in Chicago are affiliate links, and, at no cost to you, I may earn a small commission.
