$29 Cheap flight deals from Houston (HOU) to Cicero (CHI)

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This Weekend's Flight Deals from Houston to Cicero

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Jan 2 - Mon, Jan 5
IAH
George Bush Intercontinental
MDW
Midway Intl.
$363 Roundtrip, just found
$363
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Jan 2 from George Bush Intercontinental to Midway Intl., returning Mon, Jan 5, priced at $363 just found
Fri, Jan 2 - Mon, Jan 5
IAH
George Bush Intercontinental
MDW
Midway Intl.
$363 Roundtrip, just found
$363
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Jan 2 from George Bush Intercontinental to Midway Intl., returning Mon, Jan 5, priced at $363 just found
Sat, Jan 3 - Mon, Jan 5
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$382 Roundtrip, found 1 hour ago
$382
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Jan 3 from George Bush Intercontinental to O'Hare Intl., returning Mon, Jan 5, priced at $382 found 1 hour ago
Sat, Jan 3 - Mon, Jan 5
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$382 Roundtrip, found 1 hour ago
$382
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Jan 3 from George Bush Intercontinental to O'Hare Intl., returning Mon, Jan 5, priced at $382 found 1 hour ago

Airfares from $29 One Way, $58 Round Trip from Houston to Cicero

Prices starting at $58 for return flights and $29 for one-way flights to Cicero were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Feb 14 - Sat, Feb 21
IAH
Houston
ORD
Chicago
$58 Roundtrip, found 1 hour ago
$58
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Feb 14 from Houston to Chicago, returning Sat, Feb 21, priced at $58 found 1 hour ago
Wed, Jan 28 - Sat, Jan 31
IAH
Houston
ORD
Chicago
$72 Roundtrip, found 1 day ago
$72
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Jan 28 from Houston to Chicago, returning Sat, Jan 31, priced at $72 found 1 day ago
Mon, Feb 23 - Fri, Feb 27
IAH
Houston
MDW
Chicago
$84 Roundtrip, found 2 days ago
$84
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Feb 23 from Houston to Chicago, returning Fri, Feb 27, priced at $84 found 2 days ago
Wed, Feb 18 - Sat, Feb 21
IAH
Houston
ORD
Chicago
$157 Roundtrip, found 21 hours ago
$157
Roundtrip
found 21 hours ago
Select United flight, departing Wed, Feb 18 from Houston to Chicago, returning Sat, Feb 21, priced at $157 found 21 hours ago
Wed, Feb 18 - Sat, Feb 21
IAH
Houston
ORD
Chicago
$157 Roundtrip, found 21 hours ago
$157
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Wed, Feb 18 from Houston to Chicago, returning Sat, Feb 21, priced at $157 found 21 hours ago

Cicero economy flight packages

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Chicago Magnificent Mile
3.0-star property

Courtyard by Marriott Chicago Magnificent Mile

8.8/10 Excellent! (1,555 reviews)

Jan 29 - Feb 1

3 night stay

Houston (HOU) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $294, price is now $200 per person
$200
per person
found 1 day ago
Valet parking was easy and quick. The staff were all very pleasant and accommodating. The rooms were clean and the hotel overall was pleasant. Great location by restaurants and Mag Mile. Would stay again!

Reviewed on Nov 13, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,790 reviews)

Jan 29 - Feb 1

3 night stay

Houston (HOU) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $390, price is now $252 per person
$252
per person
found 1 day ago
Staff is TOP NOTCH! I am in a wheelchair right now, recovering from a knee surgery, and staff could not have been more solicitous and helpful. Also, when we checked in, upon learning of my daughter‘s birthday on Christmas, the front desk representative gave us a complementary room upgrade and sent up chocolates! The room was very clean and the shower was fantastic. Not enough good words about the buffet, as long as you’re clear that it is a “breakfast“ buffet and not a “brunch“ buffet :-). I think I was expecting a sliced roast beef and an omelette bar, but it is in fact a very extensive selection of breakfast foods. The restaurant recommendation was spot on. We had a delicious dinner of fine Mediterranean/Sardinian foodat Nora’s next door and enjoyed it immensely. I have now joined the capital RIU club and plan on spending much more time at their other properties, particularly in Costa Rica, where I am moving next month. Kudos to all, and thank you for our wonderful stay!

Reviewed on Dec 28, 2025

citizenM Chicago Downtown
4.0-star property

citizenM Chicago Downtown

9.4/10 Exceptional! (4,029 reviews)

Jan 29 - Feb 1

3 night stay

Houston (HOU) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $338, price is now $228 per person
$228
per person
found 1 day ago
Loved this hotel ! Great location!

Reviewed on Dec 16, 2025

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More About Flying To Cicero from Houston

Route Information for Flights from Houston to Cicero

Origin Airport IATA Code
HOU
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Houston to Cicero

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.