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 / 5 245 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 $56

The Talbott Hotel

4 stars
4.6 / 5 1256 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 $73

Club Quarters Wacker at Michigan

3 stars
4.0 / 5 565 reviews
Business hotel just off the Magnificent MileThe Club Quarters Wacker at Michigan Avenue hotel attends to the needs of the business traveler. Perched at a picturesque curve of Wacker Drive near the Chicago River, the hotel treats guests to professional amenities like complimentary Wi-Fi throughout the property, free use of a computer and printer, a 24-hour member service desk and concierge and ergonomic workstations in the rooms. Leisure travelers also find its close proximity to the Magnificent Mile and other Chicago attractions irresistible. Highlights 24-hour concierge and member services desk Free high-speed Internet access throughout the hotel Prime river and skyline viewsItalian restaurant on property RoomsThe Club Quarters Wacker at Michigan Avenue hotel maintains clean, basic rooms for single day, overnight and extended stays for mostly corporate clients. Some rooms have city or river views and all are equipped with ergonomic workstations, free Wi-Fi and reference books. In some studios and suites, visitors have the added conveniences of sofa beds and kitchenettes. FeaturesThe Club Quarters Wacker at Michigan Avenue hotel offers free high-speed wireless Internet access throughout the hotel, free use of a computer and printer, and meeting space for up to 1,000 guests. Guests ready for leisure time can exercise in the fitness room, or lounge in the Private Club Room (Club Quarters members only) with complimentary coffee, tea, newspapers, magazines and games. Find free, chilled bottled water is offered on each floor. TransportationO’Hare International Airport (15.6 mi/25.1 km)Midway Airport (9.5 mi/15.3 km)Blue Line (State/Lake) (0.2 mi/0.3 km)Orange Line (State/Lake) (0.2 mi/0.3 km)McCormick Place Convention Center (2.6 mi/4.1 km) Attractions Marina City (0.1 mi/0.2 km)Chicago Cultural Center (0.3 mi/0.5 km)Millennium Park (0.4 mi/0.7 km)Michigan Avenue (0.4 mi/0.7 km)Chicago Mercantile Exchange (0.5 mi/0.8 km)Board of Trade (0.7 mi/1.2 km)Tribune Tower (0.8 mi/1.2 km)Grant Park (0.8 mi/1.3 km)The Magnificent Mile (1.1 mi/1.7 km)
Value Save 12% on your stay
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Nightly rates from $77
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Cheap Flights
Departure Arrival Travel dates Round-trip
New York Chicago Sat, Feb 21 - Wed, Feb 25 $157
Los Angeles Chicago Tue, Feb 24 - Wed, Feb 25 $237
Washington DC Chicago Wed, Feb 25 - Sat, Feb 28 $98
San Francisco Chicago Wed, Mar 25 - Tue, Apr 7 $246
Newark Chicago Mon, Mar 30 - Tue, Mar 31 $199
Atlanta Chicago Tue, Feb 24 - Wed, Feb 25 $98
Seattle Chicago Tue, Mar 24 - Mon, Mar 30 $268
Boston Chicago Thu, Feb 5 - Wed, Feb 11 $155
Dallas Chicago Wed, Feb 25 - Mon, Mar 2 $107
Denver Chicago Wed, Feb 18 - Tue, Feb 24 $97
Phoenix Chicago Wed, Feb 11 - Wed, Feb 18 $117
Orlando Chicago Tue, Mar 3 - Wed, Mar 4 $160
San Juan Chicago Thu, Feb 19 - Tue, Feb 24 $332
Mexico City Chicago Thu, Feb 26 - Thu, Mar 5 $315
Philadelphia Chicago Wed, Mar 25 - Tue, Apr 7 $120
San Diego Chicago Wed, Feb 18 - Tue, Feb 24 $285
Fort Lauderdale Chicago Thu, Feb 19 - Mon, Mar 2 $137
Las Vegas Chicago Tue, Feb 24 - Mon, Mar 2 $137
Guadalajara Chicago Thu, Mar 5 - Thu, Mar 12 $350
Tampa Chicago Tue, Feb 24 - Sun, Mar 1 $145
Houston Chicago Tue, Mar 3 - Tue, Mar 17 $105
Baltimore Chicago Tue, Feb 10 - Tue, Feb 17 $117
Honolulu Chicago Wed, Feb 18 - Mon, Mar 9 $693
Orange County Chicago Tue, Feb 17 - Wed, Feb 25 $272
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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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