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

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
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $56

Hotel Rush

3 stars
4.1 / 5 175 reviews
Access to attractions, plus free Wi-Fi and indoor poolGuests at the Hotel Rush enjoy a plum location just off the Magnificent Mile. Whether the agenda is hitting downtown shops, restaurants, bars or landmarks, leisure travelers will find no shortage of distractions nearby while executives enjoy convenient access to the Loop and the Financial District. With standard amenities like complimentary Wi-Fi throughout the property, an indoor pool and fitness and business centers, the property stands as a well-rounded option for budget-minded vacationers. Highlights Close to the Magnificent MileComplimentary Wi-Fi throughout the propertyIndoor pool24-hour business centerSushi restaurant and artisan breakfast and lunch eatery onsite RoomsSmoke-free rooms at the Hotel Rush are airy and open with windows that look out to the city. Plump duvets boast a subtle beige plaid print that matches extra seating, curtains and artwork around the room. In every space, expect complimentary Wi-Fi or hardwired access, plus extras such as refrigerator, microwave, desk and free bottled water. For extra comfort, visitors can request a room with a balcony, whirlpool or wet bar. FeaturesVirtual office. Night on the town. Quick lunch. Energizing workout. Hotel Rush answers all these needs. A 24-hour business center is open for checking email, printing an agenda or sending an important document via fax. Craving a healthy snack before hitting the Magnificent Mile? Try e.leaven Food Company for artisan pastries, omelets, salads and sandwiches. For people-watching, head to Sushi Taiyo, where inventive rolls complement rice and noodle dishes. Guests whose routine requires a daily dose of cardio can work out in the 24-hour fitness center equipped with Life Fitness machines or swim laps in the indoor pool with skylights and windowed views of the city. Transportation O'Hare International Airport (17 miles)Midway Airport (13 miles)Closest train stops: Blue Line (Chicago to O'Hare) and Orange Line (Roosevelt to Midway)McCormick Place Convention Center (10 minutes) Attractions Magnificent MileRush StreetGold CoastMillennium ParkGrant ParkJohn Hancock CenterNavy Pier Business 4,000 square feet of meeting spaceCatering by Lawry's Prime Rib, e.leaven Food Company and Sushi Taiyo24-hour business centerComplimentary high-speed wired and wireless Internet access Terrace available for seasonal events Policies and feesThe lobby will undergo refurbishments from 19 January until 20 March 2015.
Value Stay 2 nights, Save 10%
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $76

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)
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $119

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
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $85

Homewood Suites Chicago Downtown

3 stars
4.4 / 5 115 reviews
Home sweet Homewood A hot breakfast. Free Wi-Fi throughout the space. Gathering with others over wine, beer and soda. These daily conveniences might be missed while on vacation, but are customary amenities at Homewood Suites Chicago Downtown. Within walking distance of the Magnificent Mile and downtown Chicago restaurants, bars and shops, the River North Hilton property prides itself on the extras--regardless of whether the trip is for business or leisure. Highlights Complimentary daily hot breakfast buffetComplimentary Wi-Fi throughout the hotelFree nightly reception with meal, beer, wine and sodaFree grocery shopping serviceKing suites with full kitchens Rooms If these weren't hotel rooms, they might pass as city condos. Each space boasts two rooms and a full kitchen that includes a two-burner stove, microwave, dishwasher and refrigerator--ideal for a family looking to save money on dining expenses or an executive on an business trip. A wall separates the living, dining and sleeping quarters to provide maximum comfort. A palette of amber, brown and burgundy warms rooms, while several wall hangings add local flavor with images of Chicago landmarks. Guests sleep on the signature, plush Homewood Sweet Dreams mattress. LCD TV, two phone lines with voicemail and complimentary local calls are standard amenities. Features Homewood Suites Chicago Downtown provides a laundry list of bonuses that come at no extra cost to visitors. Expect a daily hot breakfast buffet, Wi-Fi throughout the space, a nightly reception with meal, beer, wine and soda, free coffee, tea or hot cider in the lobby all day, a grocery shopping service and a business center. During downtime, guests head to the indoor pool and cardio center, which are blessed with panoramic views of the Chicago skyline. Transportation O'Hare International Airport (16 miles)Midway Airport (11 miles)Closest train stops: Blue Line (Clark/Lake to O'Hare) and Orange Line (State/Lake to Midway)McCormick Place Convention Center (11 minutes) Attractions Magnificent MileMuseum of Contemporary ArtNavy PierJohn Hancock CenterTribune TowerWrigley BuildingCivic Opera House Business More than 3,000 square feet of meeting spaceFree Wi-Fi throughout the hotelBusiness center with computer and printer
Value Free hot breakfast and high speed internet access
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $80
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Cheap Flights
Departure Arrival Travel dates Round-trip
New York Chicago Sat, Feb 7 - Tue, Feb 10 $87
Los Angeles Chicago Tue, Mar 17 - Wed, Mar 18 $237
Washington DC Chicago Wed, Feb 11 - Sat, Feb 14 $105
San Francisco Chicago Tue, Mar 24 - Wed, Mar 25 $245
Newark Chicago Sat, Mar 7 - Sun, Mar 15 $184
Atlanta Chicago Tue, Mar 3 - Wed, Mar 4 $107
Seattle Chicago Tue, Mar 10 - Mon, Mar 23 $282
Boston Chicago Mon, Feb 9 - Tue, Feb 10 $140
Dallas Chicago Tue, Mar 3 - Sat, Mar 7 $81
Denver Chicago Wed, Feb 11 - Tue, Feb 17 $97
Phoenix Chicago Tue, Mar 3 - Mon, Mar 9 $117
Orlando Chicago Tue, Mar 17 - Thu, Mar 19 $167
San Juan Chicago Wed, Mar 18 - Tue, Mar 31 $359
Mexico City Chicago Tue, Feb 3 - Mon, Feb 23 $336
Philadelphia Chicago Sat, Mar 14 - Tue, Mar 17 $200
San Diego Chicago Wed, Feb 11 - Tue, Feb 17 $285
Fort Lauderdale Chicago Wed, Feb 25 - Tue, Mar 3 $137
Las Vegas Chicago Wed, Feb 25 - Mon, Mar 2 $137
Guadalajara Chicago Mon, Feb 23 - Wed, Mar 18 $374
Tampa Chicago Tue, Mar 3 - Tue, Mar 10 $118
Houston Chicago Sat, Feb 7 - Tue, Feb 10 $115
Baltimore Chicago Tue, Feb 10 - Tue, Feb 17 $117
Honolulu Chicago Thu, Feb 19 - Wed, Mar 4 $673
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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