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

The Talbott Hotel

4 stars
4.6 / 5 812 reviews
The Talbott Hotel in the heart of the Gold Coast offers spacious rooms with complimentary amenities including wireless internet and access to Equinox Fitness. Located steps from Chicago's Magnificent Mile and Rush Street, the heart of Chicago's night life. Voted as an Orbitz Best of the Best hotel. The Talbott Hotel is recognized as a leader in both leisure and business travel. It offers impeccable service with its concierge staff, all Les Clefs d'Or members, to assist with your evening plans or sightseeing. After a day of excitement, relax and unwind in your oversized guest room. The elegant marble bath stocked with fine Molton Brown Bath and Spa products in your guest room or your suite. Dry off with your luxurious Frette bath linens, and sink into a terrycloth robe while enjoying a program on your 42" LCD flat screen television with 30 High Definition Channels. Nightly turndown service; we will refresh your room, turn down your bed and leave you with delectable chocolate. You will be fully rested and ready to start another day of exploration after sleeping in one of our plush pillow top beds with luxurious linens, down pillows and comforter. Another day of relaxation and luxury awaits you tomorrow Imagine the rest. * Certified "Green Seal" Hotel. * 100% of the hotels electrical carbon footprint is offset by Wind Energy. * Four Diamond Rated by AAA. * Guests must be at least 21 years of age to check in. A $20 fee per person, per night will apply to all reservations where there are more than 2 people staying in a room and will be charged directly by the hotel. Extra beds are also available upon request for a fee of $24/night. See Front Desk for more information.
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Congress Plaza Hotel at Grant Park

3 stars
3.3 / 5 818 reviews
Historic hotel on Michigan Avenue by Grant ParkGuests at the Congress Plaza Hotel at Grant Park hotel enjoy value prices and a convenient location across from Grant Park, Buckingham Fountain, Millennium Park, the Art Institute and Lake Michigan. Designed to accommodate large groups, the 850-room hotel has hosted legions of tourists, conventioneers and even the nation’s presidents since the World’s Columbian Exposition in 1893. Its presence among Chicago architecture is unmistakable: Just look for the oversized sign in all red caps. Highlights Spectacular views of Grant Park, Buckingham Fountain, Lake MichiganTwo restaurants and a lounge on site Wireless Internet in the lobby RoomsRooms at the Congress Plaza Hotel at Grant Park hotel favor space over flash. Find rooms and spacious suites of various sizes -- many with lakefront views -- as well as high ceilings and parlor seating. Wired and wireless Internet access are available for a fee. FeaturesThe Congress Plaza Hotel at Grant Park serves as a top reception site for weddings, conferences and other formal events. The lobby with its massive mosaic-tiled ceiling inspires awe in both guests and architecture fans. More than 50,000 square feet of meeting space, including the gorgeous Gold Room with its gold-leaf covered walls and ceilings, lend opulence to any occasion.Diners visit the Gazebo Restaurant, a casual restaurant serving breakfast and lunch, or Rafael's Steakhouse, a more intimate dinner venue. Cocktails and pub fare are available in the lounge.Other property amenities include a barbershop, game room and fitness center. Transportation O’Hare International Airport (16.1 mi/25.8 km) Midway Airport (8.9 mi/14.4 km) Blue Line (LaSalle) (0.9 mi/1.5 km) Orange Line (Library) (0.3 mi/0.5 km) McCormick Place Convention Center (1.7 mi/2.7 km) Nearby attractions Grant Park (across the street) State Street (0.1 mi/0.2 km)Buckingham Fountain (0.3 mi/0.5 km)The Art Institute of Chicago (0.4 mi/0.6 km)Millennium Park (0.5 mi/0.9 km)Soldier Field (1 mi/1.6 km)The Magnificent Mile (1.3 mi/2.1 km) Policies and feesValet Parking $39.00 for overnight parkingSelf-Parking $35.00 for overnight parkingIn-room wired/wireless Internet access is charged at $9.95 + tax for 24 hours.
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Nightly rates from $139

Raffaello Hotel

4 stars
4.0 / 5 145 reviews
Boutique luxury in the heart of the Gold Coast In Chicago, the rule for downtown real estate is the closer to Lake Michigan, the more posh the address. Enter the Raffaello Hotel, a four-star hotel just steps from the lake and Magnificent Mile with a Michelin-rated chef, in-room spa services, executive suites and a 24-hour business center. Blending old-world aesthetics with modern conveniences, the hotel manages luxury and intimacy while being near the downtown hub. Stepping into the vintage building just off the tourist drag, guests are more likely to feel like Gold Coast residents than tourists. Raffaello Hotel offers Drumbar, a rooftop speakeasy-style inside lounge and outdoor garden terrace, found in the 18th floor. Highlights Walk to the Magnificent MileNext to the John Hancock CenterBoutique hotel with a 24-hour business center and rooftop sundeckUpscale Italian fare at PelagoSanctuary fitness center with Precor fitness equipment RoomsStaying in this vintage building poses several advantages. The Raffaello Hotel offers rooms with high ceilings and architectural details for a unique, high-class vintage stay. Butterscotch-hued bedding and drapes match the walls, while high ceilings --painted stark white--stun with their beam construction. All rooms feature rainfall showerheads, Gilchrest and Soames amenities, 32-inch LCD TV, iHome and iPod players and 340-count linens. Rooms, which come in king, double double and suite versions are hard-wire and Wi-Fi enabled. Features Any Chicagoan will encourage a newcomer to put dining and an architectural experience on the itinerary. At the Raffaello Hotel, both needs are satisfied thanks to Pelago, the upscale Italian seafood restaurant and the rooftop garden, which is open from late spring to late fall. From the sundeck, guests can take in glorious views of the skyline, including Navy Pier and the next door neighbor: the John Hancock Center. Transportation O'Hare International Airport (18 miles)Midway Airport (12 miles)Closest train stops: Blue Line (Chicago to O'Hare) and Orange Line (Roosevelt to Midway)McCormick Place Convention Center (11 minutes) Attractions John Hancock CenterAmerican Girl PlaceMagnificent MileOak StreetNavy PierLake Michigan Business 24-hour business center with computers and printer5 meeting roomsPolycom audiovisual conferencing equipmentCatering by Pelago RistoranteWi-Fi access Policies and fees The hotel charges $24 for each additional guest.Photo identification and credit card are required at check in for incidental charges. If you do not provide a credit card, a cash security deposit in the amount of $1,000 is required.The hotel will charge $54 for valet parking and $32 for self-parking.
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Nightly rates from $109

The Whitehall Hotel

4 stars
3.8 / 5 1089 reviews
Gold Coast boutique meets 1920s charm The Whitehall Hotel manages that rare combination of location and ambiance. The hotel is situated one block from the Magnificent Mile and Rush Street nightlife district, but tucked away from the tourist fray on a residential street. One of Chicago's oldest luxury hotels but certainly no slouch, the Whitehall brims with 19th century elegance -- imagine chandeliers, wood paneling and tufted leather chairs, all restored to match the original European grace and grandeur of this Gold Coast gem. HighlightsOne block from the Magnificent Mile and Rush Street nightlifeWalk to John Hancock Center, Water Tower Place, Lake Michigan and Oak Street BeachDining at Fornetto Mei, a Pan-Italian restaurant Fitness center Rooms Chicago's independent boutique Whitehall Hotel, which has hosted guest celebrities like Katharine Hepburn, Richard Burton, Sophia Loren, Paul Newman, The Beatles and Mick Jagger over the years, provides intimate guest rooms and suites decorated with antique mahogany tables and nightstands, wood headboards, down duvets and marble bathrooms. High-speed Internet and wireless access are available in rooms (fees apply). FeaturesGuests at The Whitehall Hotel won't have to worry about leaving their dog or cat at home. The hotel welcomes pets less than 20 pounds for a non-refundable deposit. For an upscale casual dining option, dine at Fornetto Mei, which traverses Asia and Italy with its menu of oven-fired, thin crust pizza and house-made pot stickers or sample dumplings at Mei's Corner. A cozy atrium bar welcomes guests and invites sampling of the restaurant's 200 plus global and California boutique wines. Transportation O'Hare International Airport (15.3 mi/24.7 km)Chicago Midway Airport (9.7 mi/15.7 km)Blue Line (Washington/Dearborn) (1.1 mi/1.8 km)Orange Line (State/Lake) (0.9 mi/1.5 km)McCormick Place Convention Center (3.3 mi/5.3 km) AttractionsThe Magnificent Mile (0.1 mi/0.1 km)The Gold Coast (0.1 mi/0.2 km)Oak Street Beach (0.3 mi/0.4 km)Rush Street (1 block)Navy Pier (0.8 mi/1.3 km) Business Event space for six to 100 guestsBusiness center with computersHigh-speed Internet access (fees apply) Policies and feesParking fee is $49.The Whitehall Hotel is a 100% smoke free property.
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Best Western Grant Park

3 stars
3.3 / 5 273 reviews
Catch a ball game, visit major museums, relax on a budgetThe Best Western Grant Park Hotel offers visitors a great downtown location to take in all of Chicago's main attractions. Chicago's hustling and bustling Loop district, Millennium Park, Soldier Field (home of the Chicago Bears) and three of the city's most notable museums (the Art Institute of Chicago, the Adler Planetarium, Shedd Aquarium and the Field Museum of Natural History) are all within easy reach. Families will find the accommodations both comfortable and affordable. Savor a wide range of cuisines in Mei's Kitchen, where Asian, American and Italian dishes compete for guests' attention. Looking for a little exercise? Take advantage of the seasonal outdoor pool and sundeck or visit the fitness room. It's also an easy train ride away from both O'Hare and Midway Airports. Best Western Grant Park RoomsThe hotel's 172 country-themed rooms and suites are warm and inviting. Standard King Rooms contain one king-size bed, plus an in-room safe, voice mail and coffee maker. Standard Double Rooms feature the same comforts as the Standard King, but with two double beds. Lakeview rooms feature one queen bed and have impressive views of Lake Michigan and Grant Park. The Executive Rooms are fitted out for work, rest or play, and include a king bed, work desk and loveseat, refrigerator and microwave. All rooms boast pay movies, cable TV and high speed Internet. Room service is included for all guests, and there are accessible rooms available for visitors who are physically challenged. Most of the rooms are smoke-free, but there are a limited number of rooms where smoking is allowed. Reasons to Stay Comfortable guest rooms and suites for budget-conscious visitorsClose to Museum Campus, Chicago's Loop and Soldier FieldOnly seven minutes to McCormick Place Convention CenterSeasonal outdoor swimming pool and sundeck Things To Do Nearby Shedd Aquarium (0.3 mi/0.4 km)Northerly Island (0.3 mi/0.4 km)Soldier Field (0.3 mi/0.4 km)Millennium Park (0.5 mi/0.8 km)McCormick Place Convention Center (1 mi/2 km)Willis Tower (1.5 mi/2 km)Chinatown (2 mi/3 km)United Center (2 mi/3 km)Wrigley Field (3 mi/5 km) U.S. Cellular Field (3 mi/5 km)
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Cheap Flights
Departure Arrival Travel dates Round-trip
New York Chicago Tue, Jun 11 - Wed, Jun 12 $194
Los Angeles Chicago Sun, Jun 2 - Sat, Jun 8 $254
Washington DC Chicago Wed, May 29 - Tue, Jun 4 $230
San Francisco Chicago Mon, Jun 10 - Tue, Jun 11 $318
Newark Chicago Tue, Jul 2 - Wed, Jul 10 $284
Atlanta Chicago Tue, May 21 - Sat, May 25 $220
Seattle Chicago Mon, Jun 10 - Tue, Jun 18 $352
Boston Chicago Wed, May 29 - Tue, Jun 4 $143
Dallas Chicago Tue, Jun 4 - Wed, Jun 5 $168
Denver Chicago Sun, Jun 2 - Tue, Jun 4 $138
Phoenix Chicago Mon, Jun 3 - Wed, Jun 5 $276
Orlando Chicago Sat, May 25 - Wed, May 29 $128
San Juan Chicago Tue, Jul 16 - Tue, Jul 30 $479
Mexico City Chicago Mon, Jul 15 - Sun, Jul 28 $406
Philadelphia Chicago Tue, Jul 2 - Thu, Jul 11 $263
San Diego Chicago Wed, Jul 10 - Tue, Jul 16 $328
Fort Lauderdale Chicago Sat, May 25 - Wed, May 29 $128
Las Vegas Chicago Wed, May 29 - Thu, May 30 $175
Guadalajara Chicago Fri, Jun 7 - Tue, Jun 18 $368
Tampa Chicago Wed, Jul 10 - Tue, Jul 16 $238
Houston Chicago Wed, Jul 17 - Tue, Jul 23 $205
Baltimore Chicago Wed, Jun 19 - Wed, Jun 26 $300
Honolulu Chicago Wed, May 22 - Mon, May 27 $811
Orange County Chicago Tue, Jun 11 - Sun, Jun 16 $318
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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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