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.
Value Save 10% on your stay
Flight + Hotel
Book a package for more savings!
Hotel only
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
Value Save 15% On your Stay
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $125

MileNorth, A Chicago Hotel

3 stars
4.3 / 5 55 reviews
Embracing a casual chic vibe MileNorth is where the excitement of the city and warmth of home collide in the heart of Chicago. Situated just steps from the Magnificent Mile the hotel is perfectly positioned between both bustling businesses and the beautiful shores of Lake Michigan. Minutes from world class shopping museums architecture theaters and attractions such as the citys beloved Navy Pier MileNorth offers easy access to the best of Chicago from right outside its doors The 215 stylish sophisticated and spacious guestrooms at MileNorth are perfect for those who need a good nights rest before tackling the next days adventures. Rooms range from MileNorth Standard to Superior King Suites and offer refined furnishings and plenty of space for work or play. Thanks to our prime location guests know that they dont have far to go when they feel like coming back to their homebase to recover from the day. ADA accessible rooms are available to guests upon request. From craft beer to cocktails- carnitas to the signature Superior Street Burger- MileNorth Chicago has dining options to please every palate. The Barista Bar located in the lobby is the ideal place to cozy up in a corner with a cup of coffee or enjoy a glass of wine while people watching. While there are grab-and-go options the bar boasts a menu that has equally great picks for power lunches or leisurely dinners. Perched above the city on the 29th floor 52Eighty Rooftop Lounge is a chic laid-back indoor/outdoor spot perfect for toasting with signature cocktails sharing light bites and soaking in a brilliant sunset. Thanks to its panoramic views of Chicagos skyline guests can expect an overwhelming reminder that they are truly in the heart of it all.
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $126

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
Value Save 15% On Your Stay
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $130

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
Value Save 15% On Your Stay
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $138
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Cheap Flights

Departure Arrival Travel dates Round-trip
New York Chicago Sat, Sep 5 - Thu, Sep 10 $81
Los Angeles Chicago Wed, Sep 9 - Sat, Sep 12 $81
Washington DC Chicago Sun, Sep 20 - Thu, Sep 24 $158
San Francisco Chicago Wed, Sep 9 - Wed, Sep 23 $197
Newark Chicago Tue, Sep 1 - Wed, Sep 9 $167
Atlanta Chicago Thu, Aug 27 - Tue, Sep 1 $81
Seattle Chicago Tue, Sep 29 - Mon, Oct 5 $289
Boston Chicago Thu, Aug 27 - Sat, Sep 26 $81
Dallas Chicago Sat, Aug 22 - Fri, Aug 28 $81
Denver Chicago Tue, Sep 29 - Wed, Oct 7 $157
Phoenix Chicago Wed, Sep 2 - Wed, Sep 9 $177
Orlando Chicago Wed, Sep 16 - Wed, Sep 30 $118
San Juan Chicago Thu, Sep 10 - Fri, Sep 11 $295
Mexico City Chicago Wed, Aug 26 - Wed, Sep 23 $318
Philadelphia Chicago Sun, Sep 6 - Tue, Sep 8 $81
San Diego Chicago Sat, Aug 8 - Thu, Aug 20 $157
Fort Lauderdale Chicago Sat, Sep 5 - Wed, Sep 9 $117
Las Vegas Chicago Tue, Aug 25 - Mon, Aug 31 $153
Guadalajara Chicago Wed, Sep 30 - Wed, Oct 7 $413
Tampa Chicago Sat, Aug 29 - Wed, Sep 2 $117
Houston Chicago Sat, Sep 19 - Tue, Sep 22 $81
Baltimore Chicago Tue, Aug 18 - Tue, Aug 25 $97
Honolulu Chicago Tue, Aug 25 - Wed, Sep 2 $693
Orange County Chicago Tue, Aug 25 - Fri, Aug 28 $161
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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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