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

Hotel Felix

4 stars
4.2 / 5 14 reviews
Introducing the eco-friendly Hotel Felix, Chicago's all-new boutique hotel downtown is filled with unexpected delights that will leave you feeling Happy-Naturally. Hotel Felix presents an upscale and intimate luxury boutique hotel that blends a comfortable elegance with inspiring natural elements.As downtown Chicago's first hotel designed to meet Silver LEED certification, Hotel Felix delivers an enriching experience that not only benefits its guests, but the environment as well. Organic materials. Renewable resources. Even the hotel's plumbing is most impressively energy efficient. And in a city known for its green initiatives, it is the a privilege to provide an innovative, eco-friendly boutique hotel that will enhance your stay and reduce the carbon footprint. The word Felix is defined as HAPPY - which is reflective of the soothing energy and refreshing ambiance that embraces you the moment you arrive at the hotel. As you enter the hotel's architecturally unique and historic 1920s facade, you're greeted with delightful dancing waters, white marble columns and a host of services tailored to your every desire.Balancing natural elements with behind-the-scenes technologies, Hotel Felix engages your senses in a way that promises to elevate your stay. Whisper-quiet rooms blended with gentle tones and plush furnishings create an invitation to relax and escape. Schedule an appointment to unwind in its rejuvenating spa and experience professional treatments that are individually suited to your specific needs. Experience Chicago style dining at LM Bistro, a classic French bistro, serving tantalizing dishes all day long. Begin or end your evening in the chic lobby lounge, specializing in contemporary beverage creations.At Hotel Felix, you'll discover a number of amenities customized to your needs such as red carpet concierge, room service, state-of-the-art fitness center, fully-equipped professional business center, complimentary hard-wired high-speed and wireless internet service.
Value Save 15% on your stay
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Nightly rates from $80


4 stars
4.3 / 5 38 reviews
Welcome to MileNorth Chicago. Urban contemporary hotel residing in Chicago's Streeterville neighborhood. Visit MileNorth and experience high standards of service in a setting that feeds off the local energetic vibe. Hip, comfortable and sophisticated, yet down to earth. The over-sized guest rooms and suites styled with a splash of Chicago flare, showcase dreamy views which will ignite a romance with this beloved city. Enjoy the 52EIGHTY Rooftop Lounge, for a glimpse of why Chicago is known for its architecture and stunning beauty. Surrounded by highly desirable shopping, dining and entertainment such as the Magnificent Mile, Navy Pier and Millennium Park; yet also walkable to major local businesses, this 4 Star Hotel in Chicago is appealing to those looking to be productive, to dazzle or just to play.
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Nightly rates from $96

Central Loop Hotel

3 stars
4.1 / 5 38 reviews
Central Loop Hotel is located in the center of the Central Loop Chicago s downtown business district 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. Central Loop Hotel is the best value for a full service hotel in a prime city center location. Central Loop Hotel provides- Safe - restricted entry Instant registration and check out Free high speed internet access throughout the hotel Club Lounge with complimentary coffee/tea 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 24 hour guest service desk Fitness room Exercise equipment delivered to guest room upon request Corporate Apartments available Value rates
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Nightly rates from $82

The Godfrey Hotel Chicago

4 stars
4.4 / 5 11 reviews
Godfrey means peace and welcome; welcome to The Godfrey Hotel Chicago. The Godfrey Hotel Chicago offers unforgettable style from the Cubist-influenced facade to the chic accommodations, each detail of this striking new hotel has been designed with the guest's experience in mind.
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Nightly rates from $103

The Whitehall Hotel

4 stars
3.7 / 5 121 reviews
Guests at the superb Whitehall Hotel in Chicago are welcomed to an outstanding array of amenities during their stay. With 222 newly renovated rooms adorning its 21 floors, the Whitehall Hotel offers untold luxury with plush silk duvet covers, Egyptian cotton sheets, down comforters and Hypnos mattresses. Wi-Fi, cable TV and a minibar are included in each contemporary styled guest room, while the distinctive marble bathrooms ensure maximum style.   HighlightsThe hotel is in the Gold Coast district of Chicago, with choice shops like Prada and Saks just a short walk away. Situated 18 miles southeast of O’Hare International Airport (ORD) and 13 miles northeast of Midway International Airport (MDW), the hotel is in a prime location. Service is conveniently provided by Chicago’s El train from both airports into the city center, with a train stop just three blocks away from the hotel.  The Whitehall Hotel Chicago is only a four-minute walk from the Magnificent Mile and features two restaurants and a fitness center. It is a short distance away from the Water Tower Place and the Museum of Contemporary Art and less than two miles away from the majority of Chicago’s attractions including Lincoln Park Zoo, Millennium Park and Navy Pier. Guests can also enjoy exquisite Asian and Italian cuisine at the on-site Fornetto Mei.  Search ResultStay At The Whitehall Hotel in Chicago
Value Save 12% on your stay
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Nightly rates from $113
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Cheap Flights

Departure Arrival Travel dates Round-trip
New York Chicago Mon, Mar 7 - Wed, Mar 9 $81
Los Angeles Chicago Thu, Feb 25 - Wed, Mar 9 $107
Washington DC Chicago Thu, Apr 7 - Tue, Apr 12 $211
San Francisco Chicago Thu, Mar 3 - Tue, Mar 8 $188
Newark Chicago Sat, Mar 5 - Tue, Mar 8 $242
Atlanta Chicago Tue, Mar 8 - Tue, Mar 15 $81
Seattle Chicago Sat, Mar 5 - Tue, Mar 8 $233
Boston Chicago Tue, Mar 29 - Sat, Apr 2 $109
Dallas Chicago Thu, Mar 3 - Tue, Mar 8 $81
Denver Chicago Wed, Apr 6 - Wed, Apr 20 $81
Phoenix Chicago Wed, Apr 6 - Wed, Apr 13 $81
Orlando Chicago Tue, Mar 1 - Mon, Mar 7 $78
San Juan Chicago Wed, Feb 17 - Mon, Feb 29 $304
Mexico City Chicago Wed, Mar 23 - Thu, Mar 31 $293
Philadelphia Chicago Sat, Mar 5 - Thu, Mar 10 $81
San Diego Chicago Wed, Mar 2 - Tue, Mar 8 $107
Fort Lauderdale Chicago Wed, Mar 16 - Tue, Mar 29 $107
Las Vegas Chicago Sat, Feb 13 - Sun, Feb 21 $153
Guadalajara Chicago Tue, Apr 12 - Tue, Apr 19 $348
Tampa Chicago Wed, Mar 2 - Tue, Mar 8 $68
Houston Chicago Sat, Mar 5 - Tue, Mar 15 $97
Baltimore Chicago Mon, Mar 7 - Thu, Mar 10 $81
Honolulu Chicago Wed, Feb 24 - Mon, Feb 29 $656
Orange County Chicago Wed, Mar 9 - Sun, Mar 13 $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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