Short-Term Rentals in Second City, IL: Compare 10+ Sites & Save

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2369 Best Short-Term 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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Old town vintage 2 bedroom
Old town vintage 2 bedroom
Condo
Chicago, IL, 60614, United States
0.2k from Second City center

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

2 Bedrooms3 Guests
New to Booking
$100
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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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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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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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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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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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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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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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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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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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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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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Go Grand in This Massive Old Town Mansion by AllSet Turnover
Go Grand in This Massive Old Town Mansion by AllSet Turnover
Condo
Chicago, IL, 60610, United States
0.4k from Second City center

AC, Crib, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking

8 Bedrooms16 Guests
9.6

Exceptional

4 reviews

$1425
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
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 Short-Term Rentals in Second City.

Where to stay in Second City? Best neighborhoods & areas

Second City Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 2369 verified short-term rentals in Second City, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Second City vary depending on location, property size, and travel dates. Rates typically start from around $90 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Second City include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Second City, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Second City often include amenities such as Fireplace/Heating, Laundry, and Internet, providing a comfortable and convenient stay.

Short-term rentals in Second City are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.