8 Incredible Chicago Airbnbs for Every Style and Budget
Update: Some offers mentioned below are no longer available. View the current offers here: Chase Sapphire Preferred Card,Chase Sapphire Reserve
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)
1. Whit's Place in Bucktown
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.
2. Penthouse in Old Town
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.
3. Art Deco Loft
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)
4. Gold Coast Gem
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.
5. Marine Layer Loft
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)
6. Gold Coast Stunner
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.
7. Boutique-Style Guest House
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.
The Showstopper
8. Luxury Wicker Park Home
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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TPG featured card
Rewards
| 4X | Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year. |
| 4X | Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year. |
| 3X | Earn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com. |
| 2X | Earn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com. |
| 1X | Earn 1X Membership Rewards® point per dollar spent on all other eligible purchases. |
Intro offer
Annual Fee
Recommended Credit
Why We Chose It
There’s a lot to love about the Amex Gold. It’s a fan favorite thanks to its fantastic bonus-earning rates at restaurants worldwide and at U.S. supermarkets. If you’re hitting the skies soon, you’ll also earn bonus Membership Rewards points on travel. Paired with up to $120 in Uber Cash annually (for U.S. Uber rides or Uber Eats orders, card must be added to Uber app and you can redeem with any Amex card), up to $120 in annual dining statement credits to be used with eligible partners, an up to $84 Dunkin’ credit each year at U.S. Dunkin Donuts and an up to $100 Resy credit annually, there’s no reason that foodies shouldn’t add the Amex Gold to their wallet. These benefits alone are worth more than $400, which offsets the $325 annual fee on the Amex Gold card. Enrollment is required for select benefits.Pros
- 4 points per dollar spent on dining at restaurants worldwide and U.S. supermarkets (on the first $50,000 in purchases per calendar year; then 1 point per dollar spent thereafter and $25,000 in purchases per calendar year; then 1 point per dollar spent thereafter, respectively)
- 3 points per dollar spent on flights booked directly with the airline or with amextravel.com
- Packed with credits foodies will enjoy
- Solid welcome bonus
Cons
- Not as useful for those living outside the U.S.
- Some may have trouble using Uber and other dining credits
- You may be eligible for as high as 100,000 Membership Rewards® Points after you spend $6,000 in eligible purchases on your new Card in your first 6 months of Card Membership. Welcome offers vary and you may not be eligible for an offer. Apply to know if you’re approved and find out your exact welcome offer amount – all with no credit score impact. If you’re approved and choose to accept the Card, your score may be impacted.
- Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year.
- Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year.
- Earn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com.
- Earn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com.
- Earn 1X Membership Rewards® point per dollar spent on all other eligible purchases.
- $120 Uber Cash on Gold: Add your Gold Card to your Uber account and get $10 in Uber Cash each month to use on orders and rides in the U.S. when you select an American Express Card for your transaction. That’s up to $120 Uber Cash annually. Plus, after using your Uber Cash, use your Card to earn 4X Membership Rewards® points for Uber Eats purchases made with restaurants or U.S. supermarkets. Point caps and terms apply.
- $84 Dunkin' Credit: With the $84 Dunkin' Credit, you can earn up to $7 in monthly statement credits after you enroll and pay with the American Express® Gold Card at U.S. Dunkin' locations. Enrollment is required to receive this benefit.
- $100 Resy Credit: Get up to $100 in statement credits each calendar year after you pay with the American Express® Gold Card to dine at U.S. Resy restaurants or make other eligible Resy purchases. That's up to $50 in statement credits semi-annually. Enrollment required.
- $120 Dining Credit: Satisfy your cravings, sweet or savory, with the $120 Dining Credit. Earn up to $10 in statement credits monthly when you pay with the American Express® Gold Card at Grubhub, The Cheesecake Factory, Goldbelly, Wine.com, and Five Guys. Enrollment required.
- Explore over 1,000 upscale hotels worldwide with The Hotel Collection and receive a $100 credit towards eligible charges* with every booking of two nights or more through AmexTravel.com. *Eligible charges vary by property.
- No Foreign Transaction Fees.
- Annual Fee is $325.
- Terms Apply.
Rewards Rate
| 4X | Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year. |
| 4X | Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year. |
| 3X | Earn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com. |
| 2X | Earn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com. |
| 1X | Earn 1X Membership Rewards® point per dollar spent on all other eligible purchases. |
Intro Offer
You may be eligible for as high as 100,000 Membership Rewards® Points after spending $6,000 in eligible purchases on your new Card in your first 6 months of Membership. Welcome offers vary and you may not be eligible for an offer.As High As 100,000 points. Find Out Your Offer.Annual Fee
$325Recommended Credit
Credit ranges are a variation of FICO® Score 8, one of many types of credit scores lenders may use when considering your credit card application.Excellent to Good
Why We Chose It
There’s a lot to love about the Amex Gold. It’s a fan favorite thanks to its fantastic bonus-earning rates at restaurants worldwide and at U.S. supermarkets. If you’re hitting the skies soon, you’ll also earn bonus Membership Rewards points on travel. Paired with up to $120 in Uber Cash annually (for U.S. Uber rides or Uber Eats orders, card must be added to Uber app and you can redeem with any Amex card), up to $120 in annual dining statement credits to be used with eligible partners, an up to $84 Dunkin’ credit each year at U.S. Dunkin Donuts and an up to $100 Resy credit annually, there’s no reason that foodies shouldn’t add the Amex Gold to their wallet. These benefits alone are worth more than $400, which offsets the $325 annual fee on the Amex Gold card. Enrollment is required for select benefits.Pros
- 4 points per dollar spent on dining at restaurants worldwide and U.S. supermarkets (on the first $50,000 in purchases per calendar year; then 1 point per dollar spent thereafter and $25,000 in purchases per calendar year; then 1 point per dollar spent thereafter, respectively)
- 3 points per dollar spent on flights booked directly with the airline or with amextravel.com
- Packed with credits foodies will enjoy
- Solid welcome bonus
Cons
- Not as useful for those living outside the U.S.
- Some may have trouble using Uber and other dining credits
- You may be eligible for as high as 100,000 Membership Rewards® Points after you spend $6,000 in eligible purchases on your new Card in your first 6 months of Card Membership. Welcome offers vary and you may not be eligible for an offer. Apply to know if you’re approved and find out your exact welcome offer amount – all with no credit score impact. If you’re approved and choose to accept the Card, your score may be impacted.
- Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year.
- Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year.
- Earn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com.
- Earn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com.
- Earn 1X Membership Rewards® point per dollar spent on all other eligible purchases.
- $120 Uber Cash on Gold: Add your Gold Card to your Uber account and get $10 in Uber Cash each month to use on orders and rides in the U.S. when you select an American Express Card for your transaction. That’s up to $120 Uber Cash annually. Plus, after using your Uber Cash, use your Card to earn 4X Membership Rewards® points for Uber Eats purchases made with restaurants or U.S. supermarkets. Point caps and terms apply.
- $84 Dunkin' Credit: With the $84 Dunkin' Credit, you can earn up to $7 in monthly statement credits after you enroll and pay with the American Express® Gold Card at U.S. Dunkin' locations. Enrollment is required to receive this benefit.
- $100 Resy Credit: Get up to $100 in statement credits each calendar year after you pay with the American Express® Gold Card to dine at U.S. Resy restaurants or make other eligible Resy purchases. That's up to $50 in statement credits semi-annually. Enrollment required.
- $120 Dining Credit: Satisfy your cravings, sweet or savory, with the $120 Dining Credit. Earn up to $10 in statement credits monthly when you pay with the American Express® Gold Card at Grubhub, The Cheesecake Factory, Goldbelly, Wine.com, and Five Guys. Enrollment required.
- Explore over 1,000 upscale hotels worldwide with The Hotel Collection and receive a $100 credit towards eligible charges* with every booking of two nights or more through AmexTravel.com. *Eligible charges vary by property.
- No Foreign Transaction Fees.
- Annual Fee is $325.
- Terms Apply.