Vacation rentals in Chicago, Illinois

Neighborhoods in Chicago

• Wicker Park

  Indie shops, nightlife.

• Lincoln Park

  Brownstones, zoo, lake.

• The Loop

  Skyline, theaters.

• Logan Square

  Hip restaurants, boulevards.

• River North

  Galleries, steakhouses.

• Pilsen

  Mexican food, murals.

Browse by property type

• Cabins in Chicago
• Beach houses in Chicago
• Condos in Chicago
• Villas in Chicago
• Tiny homes in Chicago
• Lofts in Chicago
• Treehouses in Chicago
• A-frames in Chicago
• Yurts in Chicago
• Lakehouses in Chicago
• Ski chalets in Chicago
• Mansions in Chicago

Browse by amenity

• Chicago stays with hot tub
• Chicago stays with pool
• Chicago stays with ev charger
• Chicago stays with pet-friendly
• Chicago stays with gigabit wi-fi
• Chicago stays with dedicated workspace
• Chicago stays with fireplace
• Chicago stays with home gym
• Chicago stays with sauna
• Chicago stays with kid-friendly
• Chicago stays with bbq grill
• Chicago stays with ocean view
• Chicago stays with mountain view
• Chicago stays with lake access
• Chicago stays with ski-in / ski-out

Frequently asked questions

Are vacation rentals in Chicago cheaper than hotels?

Often yes — especially for groups of 3+ or stays of 3+ nights. Per-night rates also drop sharply with weekly and monthly discounts.

What's the best neighborhood to stay in Chicago?

It depends on your trip. We've split Chicago into neighborhood guides above so you can match vibe to itinerary.

Do I pay booking fees on StayFlow?

No. Every stay on StayFlow is direct with the host — you pay the host, not us.

Can I bring my dog to Chicago?

Yes — filter the city by Pet-friendly to see every stay that allows pets.