
Condo vacation rentals in The Loop
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Top-rated condo rentals in The Loop
Guests agree: these condos are highly rated for location, cleanliness, and more.

Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
Brand New Private Modern 2 bd 2bth apt for your stay in Chicago. We are located 2 blocks form the CTA line in the heart of Pilsen, a neighborhood Time Out labeled the 10th coolest in the world. Newly renovated, hardwood tiled floors throughout, chefs kitchen, toiletries, brand new furnishings including 2 queen beds, 1 twin sleeper, fresh linen, smart TV (HBO, Netflix, Hulu) wifi, tons of books,coloring books,board games & puzzles! We truly want you to feel like this is your home away from home.

Welcome to the Chi! Close to Downtown
Welcome to this contemporary, urban retreat in the bustling heart of River West. This entire unit is thoughtfully designed with modern convenience, catering to those seeking stylish and comfortable accommodation. This trendy unit is in a prime location, just a short walk to the Blue Line and minutes away from 90/94. With an array of restaurants, grocery markets, coffee shops, and stores within walking distance, you'll have the best of Chicago at your doorstep. 5 minute drive to United Center.

Humboldt Park Traveler's Lodge
Come stay at my gorgeous condo! Featuring exposed brick, a private entrance, stainless steel appliances, and a queen bed -> all on a quiet tree lined street! It's a perfect place to re-energize between big city adventures. Free street parking, and a 5 min walk to some of the best independently owned shops, restaurants, and bars in the city. Also, the massive and incredible Humboldt Park is also just a 5 min walk away! Please reach out for recommendations - I love giving them to people!

GLORIOUS GOLD COAST GETAWAY
Welcome! Amazing Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this apartment is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier. We look forward to hosting you!

Spacious 4 Bedroom Condo
Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ Beautiful views of Chicago ✅ Central Location ✅ Parking garage attached to the building ($15-30 / night - Operated by LAZ) ✅ FAST WIFI ✅ Comfy KING beds ✅ Shared Rooftop Deck w Grills ✅ 1 block from Red "L" subway ✅ Close proximity to Grant Park, Soldier Field, Museums

Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ Beautiful views of the Park & Lake ✅ Central Location ✅ Parking garage attached to building ($15-30 / night - Operated by LAZ) ✅ FAST WIFI ✅ Comfy KING beds ✅ Rooftop Deck ✅ 1 block from Red, Orange, Green "L" subway ✅ Close proximity to Park, Soldier Field, Museums

Lincoln Park Hideaway - 5 Min Walk to the Park!
800 sq ft 1 Bed 1 Bath Charming garden-level apartment right in the heart of Lincoln Park. Please note that you will need to walk down a short flight of stairs to access the unit. Close to all the best that Chicago has to offer! Walking distance to restaurants, convenience stores, and public transportation. Anything you could want for a nice trip to Chicago to visit friends and family, work relocation, or just explore our gorgeous city!

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)
Amazing Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this apartment is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier.

Modern Izakaya Studio in Wicker Park
Stay in a sleek underground izakaya themed studio in one of Chicago's most desirable neighborhoods. Relax and enjoy the quiet zen decor. Find our hidden Japanese whisky room. Kick back in our pillowy loungers and dig into our ramen selection... The Izakaya Studio in the heart of Wicker Park is about giving you a uniquely luxurious guest experience from which to begin your adventures in Chicago.

Lincoln Square Gem!
Very nice and updated condo in the heart of Lincoln Square! Lots of fun design elements and artwork await. This sunny condo is in the 2nd floor of a 2-flat building with friendly neighbors. My partner and I live on the first floor. You can walk to all that Lincoln Square has to offer! The Brown Line (Western stop) is just 2.5 blocks away for an easy commute to downtown!

Great location. Free parking.
Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.
Popular amenities for The Loop condo rentals
Weekly condo rentals

Int. Designer’s Lakeview Duplex w/private office

Lovely top floor 2BR/2BA, steps from everything!

Newly updated 1BD/1B in Old Irving Chicago!

Modern/Spacious 2BR/2BA West Town

East Lakeview Designer Condo with 2 Bd, 2 Bath

Near Lake Michigan & Wrigley Field

Chic Home! Walk to Nightlife-Comedy-Restaurants!

Private hot tub - King bed suite - Free parking
Pet-friendly condo rentals

Chic and Charming Vintage Condominium in Lincoln Park

Cozy Lincoln Park Condo near the lake.

Spacious 3BR • Great for Groups • Fast WiFi • Pets

Wrigley Residence in Iconic Wrigley Rooftop

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

Picture Perfect 3Bed Steps from Train and FLW

The Urban Oasis | Outdoor Lounge • Sleeps 10+

Renovated 2 Bed Condo Lincoln Park w/ Free Parking
Condo rentals with a pool

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

Just remodeled apartment close to airport and mall

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

Pond View, Washer Dryer, Non Smoking Community

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

Iconic Style, Charming Lake View
When is the best time to visit The Loop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $161 CAD | $160 CAD | $208 CAD | $212 CAD | $246 CAD | $280 CAD | $287 CAD | $268 CAD | $223 CAD | $263 CAD | $212 CAD | $217 CAD |
| Avg. temp | -3 °C | -1 °C | 4 °C | 10 °C | 16 °C | 22 °C | 25 °C | 24 °C | 20 °C | 13 °C | 6 °C | 0 °C |
Quick stats about condo rentals in The Loop

Total vacation rentals
Explore 50 vacation rentals in The Loop

Nightly prices starting at
The Loop vacation rentals start at $55 CAD per night before taxes and fees

Verified guest reviews
Over 2,150 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
50 of The Loop vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across The Loop rentals

4.8 Average rating
The Loop stays are highly rated by guests—averaging 4.8 out of 5!

Nearby attractions
The Loop’s top spots, include Millennium Park, Shedd Aquarium, and Willis Tower
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Soldier Field
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Wicker Park
- Oak Street Beach
- Lincoln Park Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Willis Tower
- Washington Park Zoo
- The 606
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