Chicago Hotels & Vacation Rentals for Thanksgiving

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Spend Thanksgiving in the Windy City

November in Chicago; where the feeling of family and fortune is never lost during the heart-warming holiday of Thanksgiving. From a variety of dining options for turkey feasts and unique Black Friday deals to family-friendly fun in the city streets, Chicago is never a city that will disappoint during the holidays.

Thanksgiving in Chicago: Top Accommodations

Apartment ∙ 4 guests ∙ 2 bedrooms
Near North, Chicago, Illinois, United States
from $175
Vrbo
5.0
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Apartment ∙ 3 guests ∙ 3 bedrooms
Hermosa, Chicago, Illinois, United States
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Vrbo
4.8
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Apartment ∙ 4 guests ∙ 2 bedrooms
Hanson Park, Chicago, Illinois, United States
from $80
Vrbo
4.8
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Apartment ∙ 4 guests ∙ 2 bedrooms
Hermosa, Chicago, Illinois, United States
from $154
Vrbo
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Apartment ∙ 2 guests ∙ 1 bedroom
Gold Coast, Chicago, Illinois, United States
from $330
Vrbo
4.8
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Apartment ∙ 2 guests ∙ 1 bedroom
Irving Woods, Chicago, Illinois, United States
from $91
Vrbo
4.9
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Apartment ∙ 4 guests ∙ 2 bedrooms
Uptown, Chicago, Illinois, United States
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Vrbo
5.0
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Apartment ∙ 2 guests ∙ 1 bedroom
Albany Park, Chicago, Illinois, United States
from $59
Vrbo
4.4
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House ∙ 4 guests ∙ 2 bedrooms
Logan Square, Chicago, Illinois, United States
from $104
Vrbo
4.8
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Where to Dine for Thanksgiving in Chicago

The Windy City has been named the top food city in America by countless sources and, really, they aren't wrong. With a wide variety of cuisine options, finding somewhere to satisfy Turkey Day hunger is not a problem at all. River North, West Loop, and even small neighborhoods offer restaurants with Thanksgiving menus worthy of your stomach!

  • 1. Tortoise Supper Club

    This classic American restaurant offers a standard Thanksgiving meal with a touch of the gourmet. At their vast buffet, you can pile all the root vegetables your heart desires next to perfectly browned turkey, oysters, and the must-have pumpkin pie. Also, cheers to a drinks list that is always seasonal.

  • 2. Grassroots

    Nestled in Southport, a small neighborhood off the CTA Brown Line, this farm-to-table restaurant will offer savory dishes sourced from their own farm in Michigan. It is a perfect spot to dine when staying at homey vacation rentals in Chicago for Thanksgiving. No matter how far from home, visitors will always feel welcome at this casual but delicious spot!

  • 3. City Mouse

    Tucked in a corner of Restaurant Row in Ace Hotel, one of the newest hotels in Chicago for Thanksgiving, City Mouse is an American establishment that offers delectable options for the hungry foodie. With turkey and lamb on the menu, no one will leave unsatisfied.

Best Places to Stay for Thanksgiving in Chicago

Private room ∙ 3 guests ∙ 1 bedroom
Brighton Park, Chicago, Illinois, United States
from $28
Airbnb
4.1
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Private room ∙ 2 guests ∙ 1 bedroom
Grand Boulevard, Chicago, Illinois, United States
from $27
Airbnb
4.5
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Private room ∙ 2 guests ∙ 1 bedroom
Bridgeport, Chicago, Illinois, United States
from $25
Airbnb
4.4
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Where to Shop on Thanksgiving Weekend in Chicago

If there’s one thing that's synonymous with Thanksgiving (other than turkey) it’s Black Friday. Luckily Chicago has a slew of options to flex that wallet power during this rush of consumer savings. Fashion outlets, the Magnificent Mile, and little boutiques in small neighborhoods all provide shoppers with ample opportunity to find that perfect holiday gift.

  • 1. Fashion Outlets of Chicago

    Just outside of the city in Rosemont, shoppers will find a treasure trove of deals at this vast outlet mall. Anchored by big names like Neiman Marcus’ Last Call, Bloomingdale’s Outlet, and Saks off 5th, there are dozens of luxury brands like Under Armour, Tory Burch, Ted Baker, and Barney’s Warehouse.

  • 2. Magnificent Mile

    Giant malls full of boutiques, luxury clothing, accessories and flagship stores (i.e. Top Shop, Anthropology, UNIQLO and Disney) flank the merrily decorated Michigan Avenue (conveniently located close to most hotels in Chicago during Thanksgiving). Shopping is almost magical when promenading with bags in-hand and Christmas lights in the air.

  • 3. Wicker Park

    Small Business Saturday is more a thing in this artsy neighborhood. Chill Fest (a line-up of live music and DJs) provide a soundtrack for shoppers as they flit in and out of boutiques, consignment shops, record stores, and product line stores like Cartharrt, Dr. Marten's, Arc'Teryx, and Fluevog Shoe Company.

Recommended Accommodations for Thanksgiving in Chicago

Private room ∙ 2 guests ∙ 1 bedroom
Hyde Park, Chicago, Illinois, United States
from $28
Airbnb
4.2
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Private room ∙ 2 guests ∙ 1 bedroom
Avondale, Chicago, Illinois, United States
from $28
Airbnb
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Private room ∙ 2 guests ∙ 1 bedroom
Albany Park, Chicago, Illinois, United States
from $17
Airbnb
4.5
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Best Activities for Families Spending Thanksgiving in Chicago

Cold weather never stops Chicago from guaranteeing a good time! Even with the holidays, the Windy City always has something fun planned for the whole family. Ice skating rinks, Christmas markets, and even parades provide great pastimes during the long weekend.

  • 1. Ice Skating

    The Chicago Park District establishes and maintains free ice rinks throughout the city for the pleasure of locals and visitors alike. With picturesque locations near Wrigley Field, University of Chicago, Cloud Gate, and Maggie Daley Park, the magic of holidays in Chicago becomes an integral part of any skater's experience.

  • 2. Christkindlmarket

    This German Christmas market has become a tradition over the past 25 years. With locations outside Wrigley Field and downtown, market-goers can purchase gifts, holiday decor, and food all while serenaded by carolers under the city lights. But the most important consumable is the mulled wine, served in a collectible mug!

  • 3. Thanksgiving Day Parade

    Certainly not equaling the grandeur of New York's parade, Chicago's Turkey Day showcase gives the Big Apple a run for its money. Visitors can watch as marching bands, large floats, and Santa Claus strut down the Magnificent Mile, officially ringing in the holiday season!

Top Offers for Thanksgiving in Chicago

Private room ∙ 2 guests ∙ 1 bedroom
West Town, Chicago, Illinois, United States
from $28
Airbnb
4.5
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Private room ∙ 2 guests ∙ 1 bedroom
East Garfield Park, Chicago, Illinois, United States
from $27
Airbnb
5.0
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Private room ∙ 2 guests ∙ 1 bedroom
West Ridge, Chicago, Illinois, United States
from $33
Airbnb
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The Weather in Chicago

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- Rainy days

Average Nightly Rental Prices in Chicago

Vacation Rental Price Information in Chicago

Vacation Rental Availability in Chicago

Rental Availability Information in Chicago

Other Popular Destinations for Thanksgiving

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