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

River Hotel

3 stars
4.2 / 5 33 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 $125

The Talbott Hotel

4 stars
4.7 / 5 75 reviews
The Talbott Hotel is a European-style resort, which is reflected by the Italian Frette linen you'll find in each of its guest rooms. This AAA Four Diamond Hotel is a member of the Historic Hotels of America, as well as being one of the first Green Seal-certified hotels in the United States, so guests can be sure that their stay will have minimal impact on the environment. HighlightsWhen guests are not relaxing in their rooms, they can easily explore the downtown Chicago area thanks to the hotel's convenient location in the Gold Coast neighborhood. Go shopping at the Magnificent Mile, or for entertainment, Drury Lane Theater is located in Water Tower Place, while the Lookingglass Theater is located next to Water Tower Place. Rush Street is just outside the doors of the hotel and is famous for its nightclubs and restaurants. The Talbott Hotel will accept up to two well-behaved dogs per room with a combined weight of 50 pounds. Luxury pet boutique Tails in the City is located just across the street. The hotel houses one on-site restaurant, the Mercadito Fish Co, but the Signature Room on 95th, Tavern on Rush, and Merlot on Maple are a few of the dining options located close to the hotel.  Search ResultStay at The Talbott Hotel in Chicago
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Nightly rates from $192

Club Quarters Wacker at Michigan

3 stars
4.2 / 5 58 reviews
Private - full service club-like hotel with 247 rooms located on the Chicago River. Just one block north of Club Quarters is the Magnificent Mile - famous for shopping. The hotel is a convenient walk to the Chicago Cultural Center - Grant Park - and Marina City. 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 maximum reception style 200 people 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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Nightly rates from $130

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 $155
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Cheap Flights

Departure Arrival Travel dates Round-trip
New York Chicago Sat, Sep 19 - Sat, Sep 26 $81
Los Angeles Chicago Wed, Aug 19 - Fri, Aug 28 $99
Washington DC Chicago Tue, Aug 18 - Wed, Sep 2 $87
San Francisco Chicago Mon, Sep 21 - Sat, Sep 26 $254
Newark Chicago Tue, Aug 18 - Wed, Aug 19 $167
Atlanta Chicago Tue, Aug 18 - Sat, Aug 22 $81
Seattle Chicago Sat, Sep 5 - Wed, Sep 9 $325
Boston Chicago Wed, Sep 9 - Sat, Sep 19 $81
Dallas Chicago Wed, Sep 9 - Wed, Sep 16 $81
Denver Chicago Tue, Sep 15 - Tue, Sep 22 $137
Phoenix Chicago Tue, Aug 25 - Tue, Sep 1 $178
Orlando Chicago Tue, Sep 1 - Wed, Sep 9 $118
San Juan Chicago Wed, Aug 26 - Wed, Sep 9 $298
Mexico City Chicago Sat, Sep 12 - Tue, Sep 22 $333
Philadelphia Chicago Sun, Aug 23 - Thu, Aug 27 $81
San Diego Chicago Tue, Sep 1 - Wed, Sep 9 $177
Fort Lauderdale Chicago Sat, Sep 19 - Tue, Sep 22 $117
Las Vegas Chicago Tue, Sep 22 - Sat, Sep 26 $156
Guadalajara Chicago Wed, Sep 16 - Sun, Sep 20 $282
Tampa Chicago Sat, Aug 29 - Wed, Sep 2 $137
Houston Chicago Sat, Sep 26 - Tue, Sep 29 $81
Baltimore Chicago Wed, Sep 16 - Tue, Sep 22 $87
Honolulu Chicago Mon, Sep 21 - Tue, Sep 29 $697
Orange County Chicago Wed, Aug 19 - Wed, Aug 26 $217
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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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