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

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771 Best Family 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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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Old Town 3bd 3ba Coach House, Garage Parking Incl
Old Town 3bd 3ba Coach House, Garage Parking Incl
House
Chicago, IL, USA
0.7k from Second City center

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

3 Bedrooms7 Guests
New to Booking
$554
Average price / night
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Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly
Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly
House
Chicago, IL, 60610, United States
0.8k from Second City center

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

3 Bedrooms14 Guests
10.0

Exceptional

5 reviews

$677
Average price / night
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Luxury Designer Penthouse | Gold Coast/Old Town
Luxury Designer Penthouse | Gold Coast/Old Town
Apartment
Chicago, IL, 60610, United States
0.8k from Second City center

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

2 Bedrooms8 Guests
9.6

Exceptional

10 reviews

$874
Average price / night
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Luxury Designer Apartment 802| Gold Coast/Old Town
Luxury Designer Apartment 802| Gold Coast/Old Town
Apartment
Chicago, IL, 60610, United States
0.8k from Second City center

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

2 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$741
Average price / night
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Level Chicago – Old Town
Level Chicago – Old Town
Apartment
1140 North Wells Street, Chicago, IL, 60610, United States
0.9k from Second City center

AC, Arcade, Barbecue, Business Services, Elevator, Fitness Equipment, Frontdesk 24 Hour, Housekeeping, Internet

1 Bedroom5 Guests
9.0

Fabulous

456 reviews

$288
Average price / night
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Luxury Designer Penthouse|Private Deck|Gold Coast
Luxury Designer Penthouse|Private Deck|Gold Coast
Apartment
Chicago, IL, 60611, United States
1.2k from Second City center

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

3 Bedrooms8 Guests
10.0

Exceptional

10 reviews

$1116
Average price / night
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 One block from Lincoln Park and the zoo
One block from Lincoln Park and the zoo
Apartment
Chicago, IL, 60614, United States
1.2k from Second City center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

1 Bedroom3 Guests
9.8

Exceptional

119 reviews

$314
Average price / night
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Private, Discreet, Luxury Chicago Gold Coast Mansion, Event-Capable.
Private, Discreet, Luxury Chicago Gold Coast Mansion, Event-Capable.
House
Chicago, IL, 60611, United States
1.2k from Second City center

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

5 Bedrooms14 Guests
10.0

Exceptional

32 reviews

$3944
Average price / night
Check Availability

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 Family Vacation Rentals in Second City.

Where to stay in Second City? Best neighborhoods & areas

Second City Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 771 verified family-friendly vacation rentals in Second City. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Second City vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $90 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Second City offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Second City are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Second City often include amenities such as Child Friendly, Fireplace/Heating, and Guest Services. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.