Cheap Chicago Vacations

Chicago

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

3 stars
3.3 / 5 153 reviews
The Congress Plaza Hotel & convention center is perfect for the value driven guest looking for a convenient downtown location with spectacular views of Grant Park, Buckingham Fountain and Lake Michigan. It is just short walk to the New Millennium Park, The Art Institute of Chicago, Museum Campus, Symphony Center, and the Sears Tower. The city business districts, shopping and restaurants, as well as downtown theaters and universities are also just minutes away. Chicago O'Hare International Airport (15 miles) and Midway Airport (11 miles) are easily accessible. The Congress Plaza Hotel & convention center was originally designed and built in 1893 to accommodate visitors to the Columbian World's Exposition. There are a total of 840 guest rooms, including 50 deluxe suites, many of which overlook the beautiful waters of Lake Michigan. Valet Parking: $33.00/night Garage Parking: $28.00/night.
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Nightly rates from $145

dana hotel and spa

4 stars
4.3 / 5 29 reviews
Located downtown in the River North neighborhood, Dana hotel and spa Chicago is the city’s ultimate boutique hotel. Luxurious furnishings and modern technology are blended with personalized service to provide guests with an experience like no other hotel in Chicago. After meetings or during a leisurely getaway, visitors are encouraged to relax and be inspired in the spa at Dana, named number 34 on Conde Nast Traveler's Top 75 U.S. Hotel Spas for 2013. The Vertigo Sky Lounge provides a spectacular view of the Chicago skyline where visitors and locals can enjoy rooftop cocktails from either an indoor or outdoor setting.  HighlightsThe hotel’s on-site Freestyle Food and Drink uses fresh, sustainable ingredients to create American dishes with a global twist. The hotel also includes a meeting room with audiovisual equipment and a fitness center with modern cardio and strength equipment. Dana Hotel and Spa Chicago sits along the Magnificent Mile and is near several major landmarks, including the Chicago Water Tower and the Michigan Avenue Bridge. Shoppers can take advantage of the close proximity of the Chicago Place Mall and the 900 North Michigan Shops, both of which are less than half a mile away. The two closest airports are O’Hare International (ORD), 15 miles from dana, and Midway International (MDW). Search ResultStay at Dana Hotel and Spa in Chicago
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Nightly rates from $158

River Hotel

3 stars
4.2 / 5 34 reviews
Boutique hotel located on the Chicago River. Just one block north is the Magnificent Mile - famous for shopping. The hotel is a convenient walk to the Chicago Cultural Center - Grant Park - and Marina City. The River Hotel provides- Safe - restricted entry Instant registration and check out Free high speed internet access throughout the hotel Club Lounge with complimentary refreshments Onsite restaurant and bar Multi-menu in room dining options through onsite restaurant bar and many local restaurants. Refrigerator and microwave available Unlimited complimentary chilled purified bottled water Meeting and event rooms available Free use of computer printer Ergonomic workstations State of the art guest rooms with premium bedding Contemporary furnishings Flat panel HD TVs Complimentary coffee and tea 24 hour guest service desk Fitness room Exercise equipment delivered to guest room upon request Corporate Apartments available
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Nightly rates from $115

Warwick Allerton Hotel Chicago

4 stars
3.9 / 5 125 reviews
As one of the first high-rises to grace Chicago's fashionable Michigan Avenue, the Warwick Allerton Hotel Chicago became synonymous with high style, luxurious hotel accommodations and impeccable service. Today, the hotel has kept the commitment to treat every guest like a celebrity and continues to make each stay at the Warwick Allerton Hotel Chicago as comfortable and rewarding as their predecessors did more than 80 years ago. Of all Magnificent Mile Chicago hotels, Warwick Allerton Hotel Chicago's historic Italian Renaissance style will dazzle you. The 443 guest rooms, including 84 suites, are perfect for your next Chicago meeting, banquet or wedding. The Warwick Allerton Hotel Chicago offers a variety of impressive, natural lit meeting rooms able to accommodate your group of 10 to 200. The Renaissance Ballroom located on the 23rd floor offers a stunning view of Michigan Avenue and Downtown Chicago. If you are looking for a luxury hotel in downtown Chicago, stay with us and experience our exquisite service and our great location. Welcome to the Warwick Allerton Hotel Chicago! Overnight valet parking $60 effective July 1st, 2013 A valid credit card must be presented at check-in for incidental charges. Early Departure Policy: Rates quoted are based on check-in date and length of stay shown. Guests checking out prior to their departure date confirmed will incur an early departure fee equal to the rate confirmed for one night.
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Nightly rates from $125

Club Quarters, Central Loop

3 stars
4.2 / 5 78 reviews
Private full service club-like hotel with 320 rooms located in the heart of Downtown Chicago Near LaSalle. It is a convenient walk to the Symphony Center - the Art Institute - The Board of Trade - the Sears Tower and Grant Park. The hotel is minutes to fine dining - shopping and entertainment. Club Quarters is the best value for a full service hotel in a prime city center location. Club Quarters provide- Safe - restricted entry Instant registration and check out Free high speed internet access throughout the hotel Club Living Room with complimentary refreshments Onsite restaurant and bar Multi-menu in room dining options through onsite restaurant bar and many local restaurants. Refrigerator and microwave available Unlimited complimentary chilled purified bottled water Meeting and event rooms available Free use of computer printer Ergonomic workstations State of the art guest rooms with premium bedding Contemporary furnishings Flat panel HD TVs Complimentary coffee and tea 24 hour guest service desk Fitness room Exercise equipment delivered to guest room upon request Corporate Apartments available Value rates Government per diem rates 365 day a year with valid id
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Hotel only
Nightly rates from $129
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Cheap Flights

Departure Arrival Travel dates Round-trip
New York Chicago Tue, Sep 29 - Wed, Sep 30 $81
Los Angeles Chicago Tue, Sep 22 - Thu, Sep 24 $97
Washington DC Chicago Wed, Sep 16 - Sat, Sep 26 $101
San Francisco Chicago Tue, Sep 15 - Wed, Sep 16 $138
Newark Chicago Wed, Oct 21 - Tue, Oct 27 $166
Atlanta Chicago Tue, Sep 29 - Tue, Oct 6 $78
Seattle Chicago Sat, Oct 10 - Sat, Oct 17 $274
Boston Chicago Sat, Sep 26 - Sat, Oct 3 $81
Dallas Chicago Sat, Oct 17 - Sat, Oct 24 $81
Denver Chicago Sat, Oct 31 - Tue, Nov 3 $81
Phoenix Chicago Sun, Sep 6 - Fri, Sep 18 $147
Orlando Chicago Tue, Sep 8 - Tue, Sep 15 $97
San Juan Chicago Mon, Oct 5 - Tue, Oct 6 $273
Mexico City Chicago Tue, Sep 22 - Sun, Oct 4 $314
Philadelphia Chicago Tue, Oct 13 - Thu, Oct 15 $81
San Diego Chicago Fri, Sep 18 - Fri, Sep 25 $89
Fort Lauderdale Chicago Tue, Nov 3 - Mon, Nov 9 $117
Las Vegas Chicago Sun, Sep 6 - Tue, Sep 8 $177
Guadalajara Chicago Fri, Sep 25 - Tue, Oct 6 $401
Tampa Chicago Wed, Nov 4 - Wed, Nov 11 $97
Houston Chicago Wed, Sep 30 - Wed, Oct 7 $87
Baltimore Chicago Wed, Sep 23 - Sat, Sep 26 $79
Honolulu Chicago Tue, Oct 20 - Tue, Oct 27 $759
Orange County Chicago Sat, Oct 17 - Tue, Oct 20 $157
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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.

  • Pancho Pistolas

    Dine out at Pancho Pistolas restaurant serving delicious Mexican cuisine in the Bridgeport neighborhood.

  • Ping Tom Memorial Park

    Admire the Oriental architecture on a steady stroll through the pleasant and quiet surroundings of Ping Tom Memorial Park.

  • Montrose Harbor

    Walk the lake-front trail north towards Montrose Harbor with some incredible views of the city skyline.

  • Alta Vista Terrace

    Capture the history of Alta Vista Terrace close to Wrigley Field, modeled on a block of row houses in London.

  • Cafe Selmarie

    Take lunch at the charming Cafe Selmarie overlooking the Lincoln Square Fountain and consume some mouth-watering cakes.

  • Chicago highlights
  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

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