Cheap Chicago Vacations
Your Chicago vacation
From food to theater and Lake Michigan to the Loop, Chicago is home to some equally big names. But you don't need to fly in on Obama's Air Force One or have pockets as deep as Oprah to be able to experience a Chicago vacation at its fullest. Take a stroll down the Magnificent Mile, catch a Cubs game at Wrigley Field, and soak up the waterfront culture of the Second City.
Before you rush to Millennium Park, allow CheapTickets to help you with the planning. We'll share the city's top highlights that will blow your mind -- without blowing your budget.
Cheap Vacation Packages
Cheap Chicago Vacation Packages
Congress Plaza Hotel at Grant Park
Flight + Hotel
Book a package for more savings!Hotel only
The Talbott Hotel
Flight + Hotel
Book a package for more savings!Hotel only
The Allerton Hotel Chicago, Magnificent Mile
Flight + Hotel
Book a package for more savings!Hotel only
The Whitehall Hotel
Flight + Hotel
Book a package for more savings!Hotel only
MileNorth, A Chicago Hotel
Flight + Hotel
Book a package for more savings!Hotel only
Cheap Flights
| Departure | Arrival | Travel dates | Round-trip |
|---|---|---|---|
| New York | Chicago | Tue, Jun 11 - Wed, Jun 12 | $158 |
| Los Angeles | Chicago | Sat, May 25 - Sat, Jun 1 | $208 |
| Washington DC | Chicago | Tue, May 21 - Tue, May 28 | $220 |
| San Francisco | Chicago | Mon, Jun 3 - Fri, Jun 7 | $318 |
| Newark | Chicago | Fri, May 10 - Tue, May 14 | $221 |
| Atlanta | Chicago | Tue, Jun 18 - Wed, Jun 26 | $220 |
| Seattle | Chicago | Fri, May 31 - Tue, Jun 4 | $318 |
| Boston | Chicago | Wed, Jun 19 - Wed, Jul 17 | $148 |
| Dallas | Chicago | Wed, Jun 5 - Tue, Jun 11 | $168 |
| Denver | Chicago | Tue, Jun 4 - Wed, Jun 5 | $128 |
| Phoenix | Chicago | Wed, Jun 5 - Tue, Jun 11 | $288 |
| Orlando | Chicago | Wed, May 15 - Mon, May 20 | $188 |
| San Juan | Chicago | Wed, Jun 5 - Wed, Jun 26 | $373 |
| Mexico City | Chicago | Sun, Jun 2 - Sun, Jun 9 | $406 |
| Philadelphia | Chicago | Mon, Jun 10 - Tue, Jun 18 | $258 |
| San Diego | Chicago | Sat, May 18 - Tue, May 21 | $305 |
| Fort Lauderdale | Chicago | Wed, May 15 - Sat, May 18 | $148 |
| Las Vegas | Chicago | Sat, Jun 1 - Tue, Jun 4 | $287 |
| Guadalajara | Chicago | Fri, Jun 28 - Sun, Jul 14 | $375 |
| Tampa | Chicago | Wed, Jun 5 - Wed, Jun 19 | $238 |
| Houston | Chicago | Sat, Jun 1 - Tue, Jun 11 | $161 |
| Baltimore | Chicago | Tue, May 28 - Wed, May 29 | $233 |
| Honolulu | Chicago | Mon, May 13 - Thu, May 23 | $811 |
| Orange County | Chicago | Mon, Jun 3 - Wed, Jun 12 | $306 |
Best time to take a vacation to Chicago
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If you visit Chicago in the early fall you will experience the best of its weather as it retains its warm temperatures but loses the humidity of the summer months. Spring time is cooler, and it is a good time to capture those cheaper flights and hotels. The Chicago Blues Festival every June attracts headline acts from around the country and is extremely popular, as is the early three-day snow sculpturing exhibition held every winter on Navy Pier. Grant Park at the harbor hosts an annual Taste of Chicago Food Festival which, as you might expect, appeals to a wide audience.
Insider tips for Chicago travel
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Pancho Pistolas
Dine out at Pancho Pistolas restaurant serving delicious Mexican cuisine in the Bridgeport neighborhood.
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Ping Tom Memorial Park
Admire the Oriental architecture on a steady stroll through the pleasant and quiet surroundings of Ping Tom Memorial Park.
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Montrose Harbor
Walk the lake-front trail north towards Montrose Harbor with some incredible views of the city skyline.
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Alta Vista Terrace
Capture the history of Alta Vista Terrace close to Wrigley Field, modeled on a block of row houses in London.
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Cafe Selmarie
Take lunch at the charming Cafe Selmarie overlooking the Lincoln Square Fountain and consume some mouth-watering cakes.
Chicago highlights
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Navy Pier
For a bustling carnival vibe along Lake Michigan, wander along the Navy Pier promenade and catch the spirit of Chicago. Bring the kids to the Children's Museum, Shakespeare Theatre or Stained Glass Gallery, and marvel at the incredible skyline views from the 150-foot Ferris wheel. Grab a bite to eat at Chicago institution Harry Caray's, and rest your weary feet to enjoy the free weekly fireworks.
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Magnificent Mile
The Mag Mile is a revered for its incredible shopping and eating scene, as well as the festivities that occur throughout the year. Lined by colorful tulips in the springtime and glittering lights during the holidays, the Mag Mile is chockablock with department stores and notable landmarks, from the Wrigley Building to Oak Street Beach. For incredible views on your Chicago travels, head to the Hancock Observatory or spend a few bucks on a cocktail in the Signature Lounge.
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Lincoln Park Zoo
For an easy escape without having to spend a cent on your Chicago travels, take the afternoon to meander through the menagerie at the Lincoln Park Zoo. Not only is it brimming with wildlife exhibits and beautiful historical architecture, it's totally free and open 365 days a year.
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Cultural Chicago
If you want to experience the cultural side of the Second City on your Chicago vacation, make a beeline for the Chicago Cultural Center where admission is free. After taking in the impressive architecture and stunning Tiffany dome, head to the Art Institute across the street to view the amazing collection of Impressionist art and the new Modern Wing. Take a stroll to the Buckingham Fountain and laze in the sun, or take in a nighttime light show.
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Millennium Park
Chicago has plenty of parks, but this one is worth a special mention. An impressive feat of engineering, landscaping and cultural celebration, Millennium Park is home to the iconic Cloud Gate sculpture and splashy Crown Fountain video sculpture. Enjoy a concert at Jay Pritzker Pavilion, the go-to spot for the best in outdoor entertainment.