Your perfect guide to the holidays in Oswego is here! Explore all the top festive events and activities. Whether you're a familiar face or a new visitor, our guide ensures you experience the holiday spirit in Oswego.
Popular Events: The enchanting Lightscape transforms the gardens into a dazzling spectacle of lights, perfect for a leisurely stroll. With its immersive displays, the Oswego Holiday Express offers a unique train ride experience that captures the magic of the season. And the Vintage Holidays in Long Grove is something you definitely don't want to miss, featuring charming shops and traditional holiday festivities. See more details on these and other fun events and activities below!
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Top Holiday Events In and Around Oswego
- Lightscape (Glencoe)
- Oswego Holiday Express
- Vintage Holidays in Long Grove (Long Grove)
- Willow Hill Lights (Northbrook)
- Randolph Street Holiday Market Festival (Chicago)
- for KING & COUNTRY: A Drummer Boy Christmas Concert (Hoffman Estates)
- Oswego Holiday Open House
- Chicago Holiday Makers Market (Chicago)
- Christmas Walk
- Coffee/Cocoa Crawl
See these and even more events listed below!
Oswego Holiday Light Displays
Lightscape
What to Expect:
Dazzling light installations and immersive soundscapes.
Description:
Lightscape at the Chicago Botanic Garden features an illuminated trail with dazzling installations, light, art, and music, creating a festive atmosphere for visitors.
Where: Glencoe | More Info: Lightscape
Willow Hill Lights
What to Expect:
Over one million LED lights and themed displays.
Description:
Willow Hill Lights is a drive-thru holiday light show at Willow Hill Golf Course in Northbrook, featuring a 2.5-mile route with over one million LED lights, three drive-through tunnels, and a 30-foot Christmas tree. The event includes themed displays like the Twelve Days of Christmas and dinosaur scenes, with holiday music playing on FM 89.9.
Where: Northbrook | More Info: Willow Hill Lights
Oswego Holiday Markets and Shopping
Randolph Street Holiday Market Festival
What to Expect:
Unique blend of vintage and modern shopping with craft cocktails and live entertainment.
Description:
Randolph Street Holiday Market Festival features 125 sellers with mini-boutiques offering posh goods for gifting, wearing, entertaining, and decorating. Enjoy craft cocktails, fancy foods, informal modeling, DJ, kids crafts, and a curated mix of vintage and modern shopping for men, women, and children.
Where: Chicago | More Info: Randolph Street Holiday Market Festival
Chicago Holiday Makers Market
What to Expect:
Unique holiday gifts from local artisans.
Description:
The Chicago Holiday Makers Market at Royal Palms Shuffleboard Club features an eclectic collection of local artisans and vendors selling vintage, handmade, and unique holiday gifts, including home goods, sweets, crafts, ornaments, jewelry, and fine art.
Where: Chicago | More Info: Chicago Holiday Makers Market
Evanston Holiday Bazaar
What to Expect:
Unique shopping experience with local artisans.
Description:
Over 50 curated vendors will showcase clothing, accessories, home goods, ceramics, glass, food, bath and body care, and more at the Evanston Holiday Bazaar. All proceeds support local nonprofits through the Community Grants Fund.
Where: Evanston | More Info: Evanston Holiday Bazaar
Oswego Holiday Shows and Entertainment
Christmas Walk
What to Expect:
Live ice sculpting and reindeer displays.
Description:
The Oswego Christmas Walk is a festive holiday event in downtown Oswego, Illinois, featuring live ice sculpting, reindeer displays, and an annual tree lighting performance. Local choirs and dance troupes perform at various locations, and children can visit Santa. The event also includes an illuminated emergency vehicle parade and decorated trucks and cars.
Where: Oswego | More Info: Christmas Walk
for KING & COUNTRY: A Drummer Boy Christmas Concert
What to Expect:
Dynamic performance by GRAMMY-winning duo.
Description:
for KING & COUNTRY brings their A Drummer Boy Christmas Tour to NOW Arena, featuring a curated selection of Christmas classics and their hit songs.
Where: Hoffman Estates | More Info: for KING & COUNTRY: A Drummer Boy Christmas Concert
Oswego Other Holiday Activities
Oswego Holiday Express
What to Expect:
Interactive holiday experience with Santa and Mrs. Claus.
Description:
Join Oswego Holiday Express at South Point for a festive journey to the North Pole. Enjoy hot cocoa from the Village Grind and meet Santa, with Mrs. Claus greeting you along the way. Each participant must be registered, and trains depart every 20 minutes.
Where: Oswego | More Info: Oswego Holiday Express
Oswego Holiday Open House
What to Expect:
Victorian Christmas decorations and gifts on display.
Description:
The Oswego Holiday Open House at the Richardson-Bates House Museum offers a Victorian Christmas experience with Christmas decorations and Victorian children's gifts on display. Visitors can explore the historic home and enjoy the festive atmosphere.
Where: Oswego | More Info: Oswego Holiday Open House
Coffee/Cocoa Crawl
What to Expect:
Sample local coffee and cocoa at various downtown shops.
Description:
Visit participating stores in downtown Aurora to enjoy a coffee and cocoa treat while exploring their amazing products.
Where: Oswego | More Info: Coffee/Cocoa Crawl
Cookie Walk
What to Expect:
Interactive cookie collection experience
Description:
Join us for the Cookie Walk, a delightful event where participants walk through a festive area while collecting cookies and enjoying holiday treats. The event features a variety of sweet and savory options, making it a fun and tasty experience for all.
Where: Oswego | More Info: Cookie Walk
Jingle Bell Jog
What to Expect:
Holiday jog with festive attire and treats.
Description:
Join the Jingle Bell Jog, a festive holiday event where participants wear Santa hats and jingle bells while jogging through downtown Oswego. Enjoy Christmas cookies and cocoa after the jog, followed by lunch and holiday shopping.
Where: Oswego | More Info: Jingle Bell Jog
Vintage Holidays in Long Grove
What to Expect:
Nostalgic holiday activities in a quaint small town setting.
Description:
Vintage Holidays in Long Grove features horse-drawn carriage rides, festive holiday carolers, and merchant specials in historic downtown Long Grove.
Where: Long Grove | More Info: Vintage Holidays in Long Grove
Festive Fun in Nearby Cities!
Discover Holiday events in hundreds of cities worldwide. Check out these nearby locations for more festive fun!
- Aurora (6 miles)
- Plainfield (9 miles)
- Batavia (12 miles)
- Naperville (13 miles)
- Romeoville (14 miles)
- Geneva (14 miles)
- Bolingbrook (15 miles)
- Crest Hill (16 miles)
- West Chicago (16 miles)
- St. Charles (16 miles)
- Woodridge (16 miles)
- Lisle (16 miles)
- Lockport (16 miles)
- Joliet (18 miles)
- Wasco (18 miles)
- Wheaton (18 miles)
- Carol Stream (19 miles)
- Downers Grove (20 miles)
- Glen Ellyn (20 miles)
- Darien (20 miles)
- Westmont (21 miles)
- South Elgin (22 miles)
- Glendale Heights (22 miles)
- Homer Glen (22 miles)
- Lombard (22 miles)
- New Lenox (23 miles)
- Bartlett (23 miles)
- Villa Park (24 miles)
- Bloomingdale (24 miles)
- Hanover Park (24 miles)
- Elgin (25 miles)
- Roselle (25 miles)
- Streamwood (25 miles)
- Addison (25 miles)
- Elmhurst (26 miles)
- Orland Park (26 miles)
- DeKalb (27 miles)
- Hoffman Estates (29 miles)
- Maywood (29 miles)
- Melrose Park (30 miles)
- Elk Grove Village (30 miles)
- Burbank (30 miles)
- Tinley Park (30 miles)
- Carpentersville (31 miles)
- Oak Lawn (31 miles)
- Berwyn (31 miles)
- Oak Forest (32 miles)
- Oak Park (32 miles)
- Rolling Meadows (33 miles)
- Cicero (33 miles)
- West Lawn (33 miles)
- Ashburn (33 miles)
- Algonquin (33 miles)
- Palatine (34 miles)
- Huntley (34 miles)
- Mount Prospect (34 miles)
- Des Plaines (34 miles)
- Chicago Lawn (34 miles)
- Lake in the Hills (34 miles)
- Belmont Cragin (35 miles)
- Gage Park (35 miles)
- Blue Island (35 miles)
- Park Ridge (35 miles)
- South Lawndale (35 miles)
- North Lawndale (35 miles)
- Brighton Park (35 miles)
- Morgan Park (35 miles)
- Portage Park (36 miles)
- West Englewood (36 miles)
- East Garfield Park (36 miles)
- Auburn Gresham (36 miles)
- Niles (37 miles)
- Harvey (37 miles)
- Irving Park (37 miles)
- New City (37 miles)
- Englewood (37 miles)
- Lower West Side (37 miles)
- Park Forest (37 miles)
- Avondale (37 miles)
- Logan Square (37 miles)
- Bridgeport (38 miles)
- West Town (38 miles)
- Albany Park (38 miles)
- Chicago (38 miles)
- Buffalo Grove (38 miles)
- Wheeling (38 miles)
- Morton Grove (38 miles)
- Chatham (38 miles)
- Greater Grand Crossing (38 miles)
- Dolton (39 miles)
- Crystal Lake (39 miles)
- South Holland (39 miles)
- Grand Boulevard (39 miles)
- Chicago Heights (39 miles)
- Douglas (39 miles)
- Near South Side (39 miles)
- Woodlawn (39 miles)
- North Center (39 miles)
- Glenview (39 miles)
- Chicago Loop (40 miles)
- Lincoln Square (40 miles)
- Hyde Park (40 miles)
- Lincoln Park (40 miles)
- Near North Side (40 miles)
- Skokie (40 miles)
- South Shore (40 miles)
- West Ridge (40 miles)
- Northbrook (41 miles)
- Uptown (41 miles)
- Edgewater (41 miles)
- South Chicago (41 miles)
- Vernon Hills (42 miles)
- Rogers Park (42 miles)
- Wilmette (42 miles)
- Calumet City (43 miles)
- Lansing (43 miles)
- Mundelein (44 miles)
- Woodstock (44 miles)
- Munster (44 miles)
- Highland Park (45 miles)