Vacation Rentals in Second City, IL: Compare 10+ Sites & Save

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2206 Best Vacation Rentals in Second City (Starting from $90)

MTM Fully Furnished Rental in Old Town - 2 beds
MTM Fully Furnished Rental in Old Town - 2 beds
Apartment
Chicago, IL, USA
0.1k from Second City center

Apartments, Cheap, Accommodations, Lodgings, Places to stay

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$90
Average price / night
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GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)
GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)
House
Chicago, IL, 60610, United States
0.0k from Second City center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms12 Guests
9.8

Exceptional

27 reviews

$1104
Average price / night
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One-of-a-Kind Apartment In Old Town!
One-of-a-Kind Apartment In Old Town!
Apartment
Chicago, IL, 60614, United States
0.1k from Second City center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Microwave

2 Bedrooms4 Guests
New to Booking
$524
Average price / night
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Top 1 Rated 4BR Lincoln Park House - King Bed
Top 1 Rated 4BR Lincoln Park House - King Bed
House
Chicago, IL, USA
0.3k from Second City center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Family

4 Bedrooms12 Guests
New to Booking
$2066
Average price / night
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Fully Furnished Rental in Old Town - 2 beds - Unit 2F
Fully Furnished Rental in Old Town - 2 beds - Unit 2F
Apartment
Chicago, IL, 60610, United States
0.1k from Second City center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, TV

2 Bedrooms5 Guests
5.2

Review score

5 reviews

$336
Average price / night
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3 br Spacious Home in Ideal Location w Free Parking Back Yard Pets Welcome
3 br Spacious Home in Ideal Location w Free Parking Back Yard Pets Welcome
House
Second City, Chicago, Illinois, USA
0.4k from Second City center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms14 Guests
New to Booking
$259
Average price / night
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Fully Furnished Rental in Old Town - 2 beds - Unit 2R
Fully Furnished Rental in Old Town - 2 beds - Unit 2R
Apartment
Chicago, IL, 60610, United States
0.1k from Second City center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, TV

2 Bedrooms5 Guests
8.8

Fabulous

5 reviews

$327
Average price / night
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5 Bedroom Huge House in Best Location Parking Fireplace Back Yard
5 Bedroom Huge House in Best Location Parking Fireplace Back Yard
House
Chicago, IL, USA
0.4k from Second City center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

5 Bedrooms22 Guests
8.3

Very Good

3 reviews

$1190
Average price / night
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Luxury SOHO Styled Two-Level Townhouse - Old Town
Luxury SOHO Styled Two-Level Townhouse - Old Town
House
Chicago, IL, 60610, United States
0.1k from Second City center

AC, Balcony, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms14 Guests
10.0

Exceptional

19 reviews

$1198
Average price / night
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The Picasso on Lincoln Park
The Picasso on Lincoln Park
Apartment
Chicago, IL, USA
0.5k from Second City center

Apartments, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

1 Bedroom2 Guests
9.0

Fabulous

1 reviews

$285
Average price / night
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4 BR • Theater Room • Gym • Walk to Lincoln Park!
4 BR • Theater Room • Gym • Walk to Lincoln Park!
House
Chicago, IL, 60614, United States
0.3k from Second City center

AC, Crib, Dryer, Fireplace, Heater, Internet, Kitchen, Microwave, No Smoking

5 Bedrooms12 Guests
New to Booking
$1346
Average price / night
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4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome
4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome
House
Chicago, IL, USA
0.5k from Second City center

Fireplace/Heating, Laundry, Breakfast, Sports/Activities, Barbecue/Outdoor Cooking, Child Friendly, Spa

4 Bedrooms18 Guests
9.6

Exceptional

5 reviews

$1199
Average price / night
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Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
House
Chicago, IL, 60610, United States
0.4k from Second City center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Heater

5 Bedrooms22 Guests
9.4

Superb

108 reviews

$1166
Average price / night
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Designer Themed 4 Bedroom in Best Location with Patio and Fireplace
Designer Themed 4 Bedroom in Best Location with Patio and Fireplace
House
Chicago, IL, USA
0.5k from Second City center

Security/Safety, Balcony/Terrace, Fireplace/Heating, Parking, Entertainment, Laundry, Breakfast

4 Bedrooms14 Guests
9.3

Superb

29 reviews

$852
Average price / night
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Gem in Heart of Chicago: Best location
Gem in Heart of Chicago: Best location
Apartment
Chicago, IL, 60610, United States
0.4k from Second City center

AC, Barbecue, Dryer, Fitness Equipment, Heater, Internet, Kitchen, Living Area, Microwave

2 Bedrooms8 Guests
10.0

Exceptional

10 reviews

$242
Average price / night
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Walk to Lincoln Park, North Avenue Beach, and Second City! Lovely Old Town Charm! condo
Walk to Lincoln Park, North Avenue Beach, and Second City! Lovely Old Town Charm! condo
Apartment
Second City, Chicago, Illinois, USA
0.5k from Second City center

Apartments, Accommodations, Lodgings, Places to stay, Family, Condos

1 Bedroom3 Guests
10.0

Exceptional

1 reviews

$371
Average price / night
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Large 4BR/3BA • Safe Old Town Location • Walk Everywhere
Large 4BR/3BA • Safe Old Town Location • Walk Everywhere
Apartment
Chicago, IL, 60610, United States
0.4k from Second City center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms15 Guests
10.0

Exceptional

74 reviews

$1153
Average price / night
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Old Town Chicago at it's finest! Pet Friendly & Recently Renovated Top-Floor Condo Has Everything You Need for a Perfect Windy City Getaway condo
Old Town Chicago at it's finest! Pet Friendly & Recently Renovated Top-Floor Condo Has Everything You Need for a Perfect Windy City Getaway condo
Apartment
Second City, Chicago, Illinois, USA
0.5k from Second City center

Apartments, Accommodations, Parking, Lodgings, Places to stay, Condos

2 Bedrooms4 Guests
New to Booking
$702
Average price / night
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Spacious 2 Bedroom unit with a Free Parking Spot
Spacious 2 Bedroom unit with a Free Parking Spot
Apartment
Chicago, IL, 60614, United States
0.4k from Second City center

AC, Crib, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
9.0

Fabulous

4 reviews

$855
Average price / night
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Large Condo with Outdoor Deck in Historic Chicago District home
Large Condo with Outdoor Deck in Historic Chicago District home
House
Second City, Chicago, Illinois, USA
0.5k from Second City center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Condos

3 Bedrooms6 Guests
New to Booking
$589
Average price / night
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Lovely 4 Bedroom Spot located in Charming Old Town
Lovely 4 Bedroom Spot located in Charming Old Town
Apartment
Chicago, IL, 60610, United States
0.4k from Second City center

AC, Crib, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms13 Guests
10.0

Exceptional

38 reviews

$1148
Average price / night
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Luxury House in the heart of Old Town with Parking
Luxury House in the heart of Old Town with Parking
House
Chicago, IL, 60610, United States
0.4k from Second City center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Elevator, Fireplace, Fitness Equipment

5 Bedrooms12 Guests
10.0

Exceptional

56 reviews

$1604
Average price / night
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GROUP LUX in Old Town/Gold Coast (+private roof)
GROUP LUX in Old Town/Gold Coast (+private roof)
Apartment
Chicago, IL, 60610, United States
0.4k from Second City center

AC, Balcony, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

6 Bedrooms12 Guests
10.0

Exceptional

6 reviews

$1397
Average price / night
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Family Friendly 2 Bedroom Full Kitchen Free Laundry Work Space
Family Friendly 2 Bedroom Full Kitchen Free Laundry Work Space
Apartment
Chicago, IL, 60614, United States
0.5k from Second City center

AC, Crib, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms5 Guests
10.0

Exceptional

3 reviews

$763
Average price / night
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Elegant 4 br Old Town Home;  Private Yard; Parking; Amazing Location
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
House
Chicago, IL, 60610, United States
0.5k from Second City center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

4 Bedrooms18 Guests
9.8

Exceptional

105 reviews

$1016
Average price / night
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Heart of the City Group Hub • Patio • Fireplace • Parking
Heart of the City Group Hub • Patio • Fireplace • Parking
House
Chicago, IL, 60610, United States
0.5k from Second City center

AC, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

4 Bedrooms14 Guests
9.2

Superb

66 reviews

$665
Average price / night
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THE COMPOUND Large Exquisite House Private Yard ''Best Location'' Well Appointed
THE COMPOUND Large Exquisite House Private Yard ''Best Location'' Well Appointed
House
Chicago, IL, 60610, United States
0.5k from Second City center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

6 Bedrooms28 Guests
10.0

Exceptional

14 reviews

$1643
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Second City.

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Frequently Asked Questions

You can explore 2206 verified vacation rentals in Second City. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Second City vary depending on the season, property size, and location. Rates typically start from around $90 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Second City include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Second City welcome pets. Currently, 48 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Second City often include amenities such as Fireplace/Heating, Laundry, and Internet. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.