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

Virgin Hotels Chicago

4 stars
Not yet reviewed
Deluxe hotel in downtown Chicago with five food and beverage venuesDiscerning travelers looking to explore bustling Chicago find strategic base at the upscale accommodations of Virgin Hotels Chicago. This centrally located hotel places holidaymakers within convenient distance to the business district and go-to points of interests including Millennium Park, Chicago Theater and the lively Navy Pier. For on-site dining options, the property features five restaurant and lounge experiences, including Miss Ricky's, a reinvented American diner, 203, a Euro-style coffee and wine bar and The Commons Club, a lounge and restaurant. Visitors can also unwind with cocktails at in-house The Rooftop Bar, offering scenic city vista. Virgin Hotels Chicago offers three flexible event venues that can host corporate and social gatherings of up to 108 people. After attending to business matters, guests can take a break by working out at the rooftop gym on site. The property also provides complimentary Wi-Fi access for added convenience. 3 Reasons To StayTwo-chamber spacesFree Wi-Fi accessMeeting venues for up to 108 people Virgin Hotels Chicago RoomsVirgin Hotels Chicago boasts modern two-chamber rooms and suites featuring separate bedroom and dressing area with closet and bathroom. All units are outfitted with sliding privacy doors, entertainment system and mini bar. Room service is also provided. Things To Do Chicago Theater (0.09 mi/0.14 km)Oriental Theater (0.2 mi/ 0.3 km)Goodman Theater (0.2 mi/ 0.3 km)Millennium Park (0.3 mi/ 0.5 km)Buckingham Fountain (0.8 mi/1.3 km)Museum of Contemporary Art, Chicago (0.8 mi/1.3 km)Navy Pier (1.0 mi/1.6 km)Shedd Aquarium (1.4 mi/2.3 km)The Field Museum (1.4 mi/2.3 km)Lincoln Park Zoo (2.4 mi/3.8 km)Wrigley Field (4.6 mi/7.4 km)
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Nightly rates from $195

Chicago's Essex Inn

3 stars
3.7 / 5 244 reviews
Affordable hotel south of Chicago's bustling downtown areaChicago's Essex Inn has an ideal location ideal on Michigan Avenue, just a few blocks south of the more congested areas of downtown Chicago. Grant Park is across the street, along with many famous Chicago attractions, including Millennium Park and the Art Institute. Sleek in design, the Essex Inn boasts a metal and glass lobby, floor-to-ceiling windows with city views and an impressive atrium housing a large pool. ADA-compliant areas are also available at Chicago's Essex Inn. Highlights Great value in the city for its location and amenitiesRooftop pool available year-roundLarge, well-equipped fitness room overlooks pool deck RoomsA color palette grounded in rich orange and brown earth tones keeps the scene warm. Floor-to-ceiling windows play up the hotel’s strongest asset, the city views. Flat-screen TVs and refrigerators are standard amenities in each room at Chicago's Essex Inn. Guests can have complimentary access to wireless Internet. Rooms also feature ADA-compliant areas. FeaturesIn a metropolis like Chicago, pools and green space are precious real estate. Chicago's Essex Inn has both. The garden pool feels like a competitive swimming complex, with a retractable atrium and global flags hanging from the rafters. The pool area features large windows that look out onto the well-manicured grounds of the rooftop garden. From the garden, guests enjoy skyline views of Grant Park and Lake Michigan from comfortable patio chairs and tables. Next to the pool is a large fitness center, featuring bikes, treadmills, weight machines, free weights, as well as six TVs.Visitors to Chicago who have come to sightsee take advantage of a hotel shuttle bus free of charge. It makes several stops along Michigan Avenue, including Water Tower Place. Other stops include Navy Pier and the Museum Campus.Travelers who want to stay connected access high-speed wireless Internet throughout hotel for a fee, or visit the 24-hour business center. Transportation O’Hare International Airport (16.1 mi/26 km) Chicago Midway Airport (8.7 mi/14.1 km) Blue Line (LaSalle to O’Hare) (3.8 mi/6.1 km) Orange Line (Roosevelt to Midway) (0.3 mi/0.5 km) McCormick Place Convention Center (1.5 mi/2.3 km) Nearby attractions Grant Park (0.5 mi/0.9 km)Millennium Park (0.8 mi/1.3 km)Lake Michigan (1.4 mi/2.2 km)The Magnificent Mile (1.5 mi/2.5 km)Museum Campus (3.1 mi/5 km) Business Six meeting rooms with space for 12 for 125 guests 24-hour business center with desktop computers, high-speed Internet access (fees apply) and a printer Complimentary high-speed wireless Internet available throughout Chicago's Essex Inn Policies and feesParking fee is $50 USD per night.
Value Save 15% on your stay
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Nightly rates from $63

The Talbott Hotel

4 stars
4.6 / 5 1253 reviews
Independently-owned and with a dedication to green practices, The Talbott Hotel has been a fixture in Chicago's Gold Coast neighborhood since 1927. The hotel mingles old-world sophistication with modern conveniences - the lobby has a cozy, open-fire warmth and the vintage-style boardrooms feature 1920s mahogany walls. Awarded the Best in Stay Award in 2014 - 2015, the Talbott features exclusive touches like the creative Tippling Brothers cocktail menu at the Mercadito Fish Co., and the knowledgeable 'Concierge Blog' on the hotel's site, setting the hotel far apart from other Chicago accommodations. Key facts149 guestroomsPets allowed (up to 50 pounds, and fees may apply)Conference and event spaces: 3 rooms, up to 200 guestsFitness centerLaundry serviceFree Wi-Fi Restaurant/bar: Mercadito Fish Co. NeighborhoodWith a prime location just a few blocks from Washington Square Park, Oak Street and the Magnificent Mile, The Talbott Hotel comes with easy access to shops like Bloomingdale's and Macy's, as well as the scenic Lakefront Trail on the shores of Lake Michigan. The Art Institute of Chicago is less than two miles from The Talbott's front entrance, boasting a staggering collection of over 250,000 works of art, including work by Vincent van Gogh, Claude Monet and Mary Cassatt. Hints and tipsFor privileged views of Chicago and a bit of distance from busy Delaware Street, ask for a room on the upper floors.For a more personalized stay, the Talbott Hotel's packages offer everything from the princess treatment for young daughters - including milk and cupcakes at turndown - to a $50 gift certificate  for the 900 North Michigan Shops. Policies and feesGuests must be at least 21 years of age to check in.
Value Last Minute Deal!
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Nightly rates from $124

Holiday Inn Express CHICAGO - MAGNIFICENT MILE

3 stars
3.7 / 5 214 reviews
Welcome to our Holiday Inn Express Magnificent Mile Hotel. Our downtown Chicago hotel , conveniently located off Michigan Avenue on the Magnificent Mile, is situated in the heart of Chicago near several businesses and attractions. Business travelers will appreciate our downtown Chicago hotel location near major companies such as Deloitte, Boeing, AT&T, Sun Microsystems, Computer Sciences Corp. and Northwestern Hospital . Flying into Chicago? Our Chicago hotel is close to O'Hare (18 miles) and Midway (12 miles) Airports, saving time for the busy executive. Staying at this landmark Chicago hotel will make it easy to visit popular Chicago attractions like the Shedd Aquarium, the Art Institute, Navy Pier, Lincoln Park Zoo and Millennium Park . Just 2 blocks away from Michigan Ave, Chicago's Magnificent Mile, where you can indulge in shopping at the Water Tower Place, Nordstrom Mall, plus more shops to choose from. The historic Holiday Inn Express Magnificent Mile hotel has 174 guestrooms and 1 suite. The public areas reflect 1920s Beaux Arts' architecture and feature a great room with comfortable seating areas for the complimentary Express Start breakfast. Our Chicago hotel provides a chic, urban setting that is Wi-Fi friendly, stylishly updated and convenient to downtown businesses and attractions. Whether you visit Chicago for business or vacation travel, stay comfortably at our Magnificent Mile hotel.
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Nightly rates from $83

SpringHill Suites by Marriott Chicago Downtown/River North

3 stars
4.1 / 5 138 reviews
A modern masterpiece in downtown Chicago SpringHill Suites Chicago Downtown/River North provides guests with a touch of luxury in the downtown Chicago area. Guests are greeted by the sweeping modern design of the lobby and can avail themselves of the many and varied facilities on offer. SpringHill Suites Chicago Downtown/River North offers a breakfast bar, a fully equipped business facility and local restaurant delivery service. The goal of the hotel is to ensure the needs of each guest are met. In addition, guests will love the close proximity to boutiques and art centers. 3 Reasons To Stay Close proximity to all of the landmarks in Chicago, including the Magnificent Mile Grab n' Go Breakfast available daily, which is convenient for guests in a hurry Indoor bubbling swimming pool on the 27th floor of the hotel SpringHill Suites Chicago Downtown/River North Rooms Suites at the SpringHill Suites Chicago Downtown/River North are roomy and modern, with sleek modern furniture throughout. Look for the large windows in each suite, which offer sweeping views of the River North area. Rooms have crisp linens, custom-made comforters, and thick mattresses. A selection of down, feather and foam pillows are available as needed. Guests also enjoy full climate control and air conditioning in their suites. Each suite features full ironing facilities, an alarm clock and a coffee-maker. Suites also have kitchens equipped with many amenities including a microwave and mini-fridge. Guests can also relax and enjoy in-room entertainment with large flat-screen televisions in every suite. Business travelers will find in-suite features such as high speed Wi-Fi accessibility, desk-level power outputs, and phones equipped with voice mail and speakerphone facilities. Business guests at SpringHill Suites Chicago Downtown/River North will also appreciate the numerous facilities available within the on-site business center. Things To Do Art Institute of Chicago (0.9 mi/1.4 km) John Hancock Observatory (1.6 mi/2.6 km) John G. Shedd Aquarium (2.9 mi/4.6 km) Adler Planetarium (3.4 mi/5.4 km) Museum of Science and Industry (8.6 mi/13.8 km)
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Nightly rates from $109
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Cheap Flights
Departure Arrival Travel dates Round-trip
New York Chicago Sat, Feb 7 - Sat, Feb 14 $87
Los Angeles Chicago Tue, Feb 10 - Wed, Feb 11 $210
Washington DC Chicago Wed, Feb 4 - Sat, Feb 7 $112
San Francisco Chicago Tue, Mar 24 - Mon, Mar 30 $246
Newark Chicago Sat, Feb 21 - Wed, Feb 25 $177
Atlanta Chicago Wed, Feb 4 - Wed, Feb 11 $78
Seattle Chicago Wed, Feb 25 - Wed, Mar 4 $289
Boston Chicago Mon, Feb 2 - Tue, Feb 3 $155
Dallas Chicago Sat, Feb 28 - Wed, Mar 4 $107
Denver Chicago Wed, Feb 18 - Tue, Feb 24 $97
Phoenix Chicago Tue, Feb 10 - Wed, Feb 18 $137
Orlando Chicago Wed, Feb 11 - Sun, Feb 22 $145
San Juan Chicago Mon, Feb 2 - Mon, Feb 9 $332
Mexico City Chicago Sat, Mar 14 - Tue, Mar 17 $407
Philadelphia Chicago Mon, Mar 2 - Wed, Mar 4 $269
San Diego Chicago Wed, Mar 25 - Tue, Apr 7 $285
Fort Lauderdale Chicago Wed, Feb 25 - Tue, Mar 3 $137
Las Vegas Chicago Wed, Mar 4 - Wed, Mar 11 $137
Guadalajara Chicago Tue, Mar 3 - Wed, Mar 18 $421
Tampa Chicago Tue, Feb 3 - Sun, Feb 8 $149
Houston Chicago Sat, Feb 7 - Sat, Feb 14 $125
Baltimore Chicago Tue, Mar 3 - Tue, Mar 17 $117
Honolulu Chicago Mon, Jan 26 - Sat, Jan 31 $850
Orange County Chicago Wed, Feb 4 - Sat, Feb 14 $297
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Best time to take a vacation to Chicago

  • 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

  • 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

  • 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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