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
The Talbott Hotel
Flight + Hotel
Book a package for more savings!Hotel only
Congress Plaza Hotel at Grant Park
Flight + Hotel
Book a package for more savings!Hotel only
Raffaello Hotel
Flight + Hotel
Book a package for more savings!Hotel only
Best Western Grant Park
Flight + Hotel
Book a package for more savings!Hotel only
The Whitehall Hotel
Flight + Hotel
Book a package for more savings!Hotel only
Cheap Flights
| Departure | Arrival | Travel dates | Round-trip |
|---|---|---|---|
| New York | Chicago | Tue, Jul 30 - Thu, Aug 29 | $201 |
| Los Angeles | Chicago | Fri, Aug 2 - Mon, Aug 19 | $298 |
| Washington DC | Chicago | Sat, Jun 8 - Tue, Jun 11 | $188 |
| San Francisco | Chicago | Thu, Aug 1 - Mon, Aug 26 | $358 |
| Newark | Chicago | Fri, Jun 7 - Tue, Jun 11 | $221 |
| Atlanta | Chicago | Sat, Jun 22 - Tue, Jun 25 | $220 |
| Seattle | Chicago | Wed, Jul 31 - Thu, Aug 15 | $368 |
| Boston | Chicago | Tue, Jul 30 - Sat, Aug 24 | $163 |
| Dallas | Chicago | Wed, Jun 26 - Tue, Jul 2 | $216 |
| Denver | Chicago | Wed, Jul 17 - Thu, Jul 25 | $138 |
| Phoenix | Chicago | Sat, Jul 13 - Thu, Jul 25 | $295 |
| Orlando | Chicago | Wed, Jul 24 - Wed, Jul 31 | $236 |
| San Juan | Chicago | Wed, Jul 31 - Wed, Aug 7 | $479 |
| Mexico City | Chicago | Fri, Jul 5 - Fri, Jul 19 | $356 |
| Philadelphia | Chicago | Tue, Jul 2 - Tue, Jul 9 | $278 |
| San Diego | Chicago | Tue, Jul 30 - Tue, Aug 13 | $288 |
| Fort Lauderdale | Chicago | Thu, Jul 4 - Wed, Jul 10 | $254 |
| Las Vegas | Chicago | Wed, Jun 12 - Sun, Jun 16 | $268 |
| Guadalajara | Chicago | Mon, Jun 17 - Fri, Jul 5 | $562 |
| Tampa | Chicago | Wed, Jul 17 - Wed, Jul 24 | $238 |
| Houston | Chicago | Sun, Jul 28 - Thu, Aug 1 | $215 |
| Baltimore | Chicago | Mon, Jun 17 - Tue, Jun 18 | $242 |
| Honolulu | Chicago | Tue, Jul 30 - Wed, Aug 14 | $843 |
| Orange County | Chicago | Tue, Jul 9 - Wed, Jul 10 | $353 |
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.